Herbicidal sulfonylureas

ABSTRACT

Novel substituted N-sulfonyl-N&#39;-pyrimidinylureas or N-sulfonyl-N&#39;-triazinylureas of the formula I ##STR1## have good pre- and postemergence selective herbicidal and growth regulating properties. 
     In this formula 
     E is nitrogen or --CH═, 
     the group ##STR2##  is a phenyl, naphthyl, furyl, thiophenyl, pyrrole or pyridinyl radical which is substituted in accordance with the definitions of 
     R 1  and R 2 , 
     R 3  and R 4  are hydrogen, lower alkyl or lower alkoxy, or one of R 3  and R 4  may also be halogen, lower alkenyl, lower haloalkenyl, lower haloalkoxy, amino, lower alkylamino, --CH(OCH 3 ) 2 , a cyclized ketal group or a saturated 5- or 7-membered heterocycle which is bound through the nitrogen atom, 
     R 5  is hydrogen, lower alkyl, lower haloalkyl, or an unsubstituted or substituted phenyl, benzyl or naphthyl radical, and 
     R 6  is an alkyl, acyl or acylamido radical which is bound through sulfur or a sulfinyl or sulfonyl group and is as defined in the description, or is a 5- to 7-membered heterocyclic amino radical which is bound through the nitrogen atom. 
     These compounds are particularly suitable for selectively controlling weeds in crops of cereals.

This is a division of application Ser. No. 053,912, filed 5/26/87, now U.S. Pat. No. 4,764,203, which is a division of application Ser. No. 699,388, filed 2/7/85, now U.S. Pat. No. 4,685,961.

The present invention relates to novel substituted N-sulfonyl-N'-pyrimidinylureas and N-sulfonyl-N'-triazinylureas and salts thereof with herbicidal and plant growth regulating properties, to the preparation thereof, to compositions containing them and to the use thereof for controlling weeds, in particular selectively, in crops of useful plants, or for regulating and inhibiting plant growth. The invention further relates to novel pyrimidin-2-ylureas and triazin-ylalkylamines prepared as intermediates.

The substituted N-sulfonyl-N'pyrimidinylureas and N-sulfonyl-N'-triazinylureas of this invention have the formula I ##STR3## wherein E is nitrogen or --CH═,

X is oxygen, sulfur, --NR⁷, --N═CR⁷, --CH═CH-- or ##STR4## Y is oxygen or an S(O)_(m) radical, m is 0 or an integer from 1 to 2,

Z is oxygen or sulfur,

R¹ is hydrogen, halogen, nitro, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₂ -C₄ alk kenyl, C₂ -C₄ haloalkenyl, C₂ -C₄ alkynyl, an amino group NR¹⁰ R¹¹, a ketal radical --CR⁷ (OC₁ -C₇ alkyl)₂ or ##STR5## a tetrahydrofuran-2-yloxy or tetrahydropyran-2-yloxy radical, --OSO₂ R⁸, --COR⁸, ##STR6## --SO₂ NR¹⁰ R¹¹, SO₂ R⁸, YR⁸, phenyl, benzyl or phenoxy, wherein the phenyl nucleus can be substituted by one or more identical or different members selected from the group consisting of halogen, nitro, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy,

R² is hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl or nitro,

R³ and R⁴, each independently of the other, are hydrogen, halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkoxyalkoxy, cyclopropyl, NH₂, C₁ -C₄ alkylamino, di(C₁ -C₄)alkylamino or a 5- to 7-membered nitrogen-containing heterocycle which is bound through the nitrogen atom and which may contain a further hetero atom, or are a --CH(OCH₃)₂ or ##STR7## radical, R⁵ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, or a phenyl, benzyl, furyl, thienyl or naphthyl radical, each of which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of halogen, nitro, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy,

R⁶ is an --S(O)_(m) R⁹ radical or a 5- to 7-membered heterocyclic radical which is bound through a nitrogen atom and may contain further hetero atoms in the ring and may be fused to a benzene ring and is unsubstituted or substituted by one or more identical or different members selected from the group consisting of nitro, halogen or C₁ -C₄ alkyl,

R⁷ is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₅ -C₆ 6cycloalkyl, C₄ -C₇ cycloalkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkenyl, C₂ -C₄ haloalkenyl, C₅ -C₆ cycloalkenyl, C₃ -C₄ alkynyl, C₁ -C₄ cyanoalkyl, C₁ -C₄ alkyl-NR⁹ R¹⁰, benzyl or benzyl which is substituted by halogen,

R⁸ is C₁ -C₄ alkoxy or has the same meaning as R⁷ but is not hydrogen,

R⁹ is a C₁ -C₄ alkyl radical which can be substituted by halogen, C₂ -C₄ alkoxy, carboxyl, C₁ -C₄ alkoxycarbonyl or --CONR¹⁰ R¹¹, or is a phenyl, benzyl or naphthyl radical, each of which can be substtiuted by one or more identical or different members selected from the group consisting of halogen, nitro, carboxyl, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy, and in an --SR⁹ radical R⁹ can also be a radical selected from --CZ--C₁ -C₄ alkyl, --CZO--C₁ -C₄ alkyl, --CZNR¹⁰ R¹¹, --CZ-phenyl, CZ-benzyl or CZ-naphthyl, wherein the phenyl rings may be substituted as indicated above,

R¹⁰ and R¹¹, each independently of the other, are hydrogen, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₁ -C₄ cyanoalkyl, or one of R¹⁰ and R¹¹ may also be C₁ -C₄ alkoxy or C₂ -C₄ alkoxyalkyl, phenyl or benzyl, and the phenyl ring may be substituted by one or identical or different members selected from the group consisting of halogen, nitro, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy; or R¹⁰ and R¹¹, together with the nitrogen atom to which they are attached, may also be a 5- to 7-membered saturated or partially saturated heterocycle which may contain a further nitrogen or sulfur atom in the ring and/or one or two further nitrogen atoms, and which may be substituted by halogen and/or C₁ -C₄ alkyl.

The invention also relates to the salts of these sulfonylureas with organic and inorganic bases.

Herbicidal ureas, triazines and pyrimidines are generally known in the art. Sulfonylureas with herbicidal and plant growth regulating properties have recently been described for example in European patent applications 44211, 44807 and 44808, and also in UK patent applications 2 112 783 and 2 112 784.

Alkyl in the above definitions denotes straight chain or branched alkyl, for example methyl, ethyl, n-propyl, isopropyl or the 4 isomers of butyl.

Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, the 4 isomers of butoxy, n-amyloxy, isoamyloxy, 2-amyloxy or 3-amyloxy, with methoxy, ethoxy or isopropoxy being preferred.

Halogen by itself or as moiety of haloalkoxy, haloalkyl or haloalkylthio denotes fluorine, chlorine and bromine, with fluorine and chlorine being preferred.

Within the scope of this invention, the radicals defined for R⁶ comprise for example the following radicals:

    __________________________________________________________________________     --S--C.sub.1 -C.sub.4 alkyl                                                               --S--CH.sub.2 COOC.sub.1 -C.sub.4 alkyl                                                      phenylthio-SCH.sub. 2 COOH                            --SO--C.sub.1 -C.sub.4 alkyl                                                              --S--CH.sub.2 CONHC.sub.1 -C.sub.4 alkyl                                                     benzylthio-SCH(CH.sub. 3)COOH                         --SO.sub.2 C.sub.1 -C.sub.4 alkyl                                                         --S--CH.sub.2 CON(C.sub.1 -C.sub.4 alkyl).sub.2                                              benzoylthio                                           --S--CO--C.sub.1 -C.sub.4 alkyl                                                           --S--CS--OC.sub.1 -C.sub.4 alkyl                                                             --SCSN(C.sub.1 -C.sub.4 alkyl).sub.2                  __________________________________________________________________________

as well as the following heterocyclic amino radicals: 1,2,4-triazolyl, 1,2,3,4-tetrazol-1-yl, pyrazol-1-yl, imidazol-1-yl, benztriazol-1-yl, benzimidazol-1-yl, indol-1-yl, indadzol-1-yl, pyrimidin-1-yl, pyridazin-1-yl, pyrazin-1-yl, which rings may be substituted by one to three members selected from nitro, halogen, preferably chlorine or bromine, and/or C₁ -C₄ alkyl, preferably methyl.

The 5- to 7-membered saturated or partially saturated heterocyclic radicals falling within the definition of the amino radical NR¹⁰ R¹¹ comprise for example the following radicals: pyrrolidino, piperidino, morpholino, thiomorpholino, azepino, imidazol-1-yl, triazol-1-yl, 1,3-oxazol-3-yl, 1,3-thiazol-1-yl, piperazin-1-yl, which radicals may be unsubstituted or sdubstituted by halogen, preferably chlorine or bromine and/or by C₁ -C₄ alkyl, preferably methyl.

Alkoxyalkyl radicals are methoxymethyl, ethoxymethyl, methoxyethyl and ethoxyethyl, with methoxyethyl being preferred. Within the scope of this invention, alkoxyalkyl radicals are methoxymethoxy, ethoxymethoxy, methoxyethoxy and ethoxyethoxy. Haloalkyl by itself or as moiety of another substituent such as haloalkoxy or haloalkylthio is usually chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1,1,2-trifluoro-2-chloroethyl, 2,2,2-trifluoro-1,1-dichloroethyl, pentachloroethyl, 3,3,3-trifluoropropyl, 2,3-dichloropropyl, and 1,1,2,3,3,3-hexafluoropropyl. Fluoromethyl, chloromethyl, difluoromethyl and trifluoromethyl are preferred.

Preferred compounds of formula I are those wherein either

Z is an oxygen atom,

the ##STR8## radical is a phenyl radical which is substituted in the ortho-position by R¹,

R⁶ is an --S(O)_(m) R⁸ radical,

R⁶ is a 5- to 7-membered heterocycle which is bound through the nitrogen atom and may contain further hetero atoms in the ring, and may be fused to a benzene ring and may be unsubstituted or substituted by one or more members selected from the group consisting of nitro, halogen and/or C₁ -C₄ alkyl.

Preferred compounds are for example those of the formula Ic ##STR9## wherein E, R¹, R³, R⁴ and R⁶ are as defined for formula I; and those of the general formula Id ##STR10## wherein E, R³, R⁴, R⁵, R⁶ and R⁸ are as defined for formula I.

The compounds of formula I are prepared for example by the following methods.

A first process comprises reacting a sulfonyl isocyanate of formula II ##STR11## wherein R¹, R², X and Z are as defined for formula I, with the equivalent amount of a 2-aminopyrimidine or 2-aminotriazine of formula III ##STR12## wherein E, R³, R⁴, R⁵ and R⁶ are as defined for formula I, in an inert organic solvent or diluent, and, if desired, isolating the resultant urea in the form of a salt or converting it into a salt with an inorganic or organic base.

A second process for obtaining the compounds of formula I comprises reacting a sulfonylamide of formula IV ##STR13## wherein R¹, R² and X are as defined for formula I, with the equivalent amount of a 2-pyrimidinyl- or 2-triazinylcarbamoylhalide of formula V ##STR14## wherein Hal is a halogen atom, preferably chlorine or bromine, and E, R³, R⁴, R⁵, R⁶ and Z are as defined for formula I, in an inert solvent or diluent and in the presence of a base, and, if desired, isolating the resultant urea in the form of a salt or converting it into a salt with an inorganic or organic base.

A third process for obtaining the compounds of formula I comprises reacting a sulfonylurea of formula VI ##STR15## wherein E, R¹, R², R³, R⁴, X and Z are as defined for formula I, with the equivalent amount of a methyl halide of formula VII ##STR16## wherein Hal is a halogen atom, preferably a chlorine or bromine atom, and R⁵ and R⁶ are as defined for formula I, in an inert solvent or diluent and in the presence of a base, and, if desired, isolating the resultant urea in the form of a salt or converting it into a salt with an inorganic or organic base.

If desired, the ureas of formula I can be converted into basic addition salts with amines, alkali metal hydroxides or alkaline earth metal hydroxides or with quaternary ammonium bases. This is done for example by reacting the urea with the equimolar amount of base and removing the solvent by evaporation. Such reactions are known and are described for example in U.S. Pat. Nos. 2 834 757 and 3 410 887.

It is convenient to carry out these reactions for obtaining compounds of formula I in aprotic, inert organic solvents.

Examples of such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane; chlorinated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, or chlorobenzene; ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxan; nitriles such as acetonitrile or propionitrile; amides such as dimethylformamide, diethylformamide or N-methylpyrrolidinone.

The reaction temperatures are preferably in the range from -20° to +120° C. The coupling reactions are normally slightly exothermic and can be carried out at room temperature. To shorten the reaction time or also to initiate the reaction it is expedient to heat the reaction mixture briefly to boiling point. The reaction times can also be shortened by addition of a few drops of a base or isocyanate as catalyst. Preferred bases are tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo[2,2,2]octane, 1,5-diazabicyclo[4,3,0]-non-5-ene or 1,8-diazabicyclo[5,4,0]undec-7-ene. However, the bases employed may also be inorganic bases, e.g. hydrides such as sodium hydride or calcium hydride, hydroxides such as sodium hydroxide or potassium hydroxide, carbonates such as sodium or potassium carbonate, or bicarbonates, such as potassium or sodium bicarbonate.

The final products of formula I can be isolated by concentrating the reaction mixture and/or removing the solvent by evaporation, and by recrystallisation or by triturating the solid residue in a solvent in which it is poorly soluble, such as an ether, an aromatic hydrocarbon or a chlorinated hydrocarbon.

In addition to these general methods of preparing the compounds of formula I, and depending on the meanings of the substituents R⁵ and R⁶, further synthesis paths, each of which is suitable only for one specific group of final products, are also possible. Such syntheses are illustrated in the following schemes. In the formulae below, E, m, R¹, R², R³, R⁴, R⁵, R⁶, R⁸, X and Z are as defined for formula I. The Roman numerals I, II and IV denote the formulae so numbered above. ##STR17##

A 2-aminopyridine or a 2-amino-1,3,5-triazine of formula VIII is condensed with an aldehyde to give the Schiff's base, which is reacted in situ with the mercapto compound. The reaction is carried out at elevated temperature, for example at the boiliong point of the reaction mixture in an organic solvent or mixture of solvents, e.g. an alkanol and/or an aromatic hydrocarbon. A small amount of catalyst is added to accelerate the reaction. Example 1 describes the preparation of a compound of the formula IIIa and further compounds are listed in Table 1. These intermediates are novel and constitute an object of the invention. The condensates of formula IIIa are then reacted, in accordance with the first preparatory process, with a sulfonyl isocyanate of formula II, as described in Examples 9-11. ##STR18##

In this process also the 2-aminopyridine or 2-aminotriazine of formula VIII is reacted with a cyclic secondary amine. The reaction is conducted in the presence of a small amount of acid in an organic solovent. Examples 5-8 describe such reactions to give compounds of the formula IIIb. These compounds can then be further reacted with a sulfonyl isocyanate of formula II to give an urea of formula I, as described in Examples 12 and 13. ##STR19##

The 2-aminopyrimidine or 2-aminotriazine of formula VIII and a sulfinic acid are charged to an organic solvent or diluent and the mixture is heated to give the aldehyde. The condensate can be precipitated by diluting the reaction mixture with water. Such a reaction is described in Example 2. Further compounds are listed in Table 2. The intermediates of formula IIIc likewise constitute an object of this invention. The further reaction of the compound of formula IIIc with a sulfonyl isocyanate of formula II to give the urea of formula I is performed in known manner.

A compound of formula IIIa can also be converted by oxidation into a compound of formula IIIc ##STR20## wherein n is 1 or 2.

The oxidation is carried out in an inert solvent or diluent in the temperature range from 0° C. to the boiling point of the reaction mixture. Suitable oxidising agents are hydrogen peroxide, an organic peracid such as perbenzoic acid or peracetic acid, or also potassium permanganate or chromium oxide. The duration of the oxidation and the amount of oxidising agent to be used depend on the desired oxidation step of the compound of formula IIIa. ##STR21##

This scheme corresponds more or less to the above described second process for the preparation of the sulfonylureas of formula I, except that first a (2-pyrimidinyl)-N-methylcarbamoyl halide or N-(2-triazinyl)-N-methylcarbamoyl halide of the formula Va is prepared in a preliminary step, in an inert organic solvent, by condensing the compound of formula III with a carbonyl dihalide (phosgene), and then reacting the compound of formula Va with the sulfonamide of formula IV to give an urea of formula I. ##STR22##

A sulfonyl halide of formula IV is reacted with a methyl halide, in an inert organic solvent and in the presence of a base, to give an urea of formula I. The reaction takes place at room temperature and can be speeded up by heating briefly to the boiling point of the reaction mixture. ##STR23##

This schema is the same as scheme 1, except that a sulfonylurea of formula XI is used as starting material. This sulfonylurea is then reacted with an aldehyde and a mercaptan in an inert organic solvent or diluent and in the presence of a small amount of acid. The resultant sulfonylurea of formula Ia can be oxidized to give the corresponding sulfinyl or sulfonyl compound of formula Ib by an oxidation similar to that described after scheme III. ##STR24##

This scheme is similar to scheme 2, except that the starting material employed is a sulfonylurea of formula IX, which is then reacted, in an inert solvent or diluent, with an aldehyde and a cyclic secondary amine, in the presence of a small amount of acid and at elevated temperature, to give an sulfonylurea of formula I.

The final products can be isolated by concentrating the reaction mixture and/or evaporating off the solvent, and purified by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, e.g. in an ether, an aromatic hydrocarbon or a chlorinated hydrocarbon.

The compounds of formula I are stable compounds, and no protective measures are required for handling them.

When used at low rates of application, the compounds of formula I have good selective growth inhibiting and selective herbicidal properties which make them most suitable for use in crops of useful plants, especially in cereals, cotton, soybeans, maize and rice. In some cases damage is also caused to weeds which have only been controlled up to now with total herbicides.

The mode of action of these compounds is unusual. Many are translocatable, i.e. they are absorbed by the plant and transported to other parts of it where they then exert their action. Thus, for example, it is possible to damage perennial weeds to the roots by surface treatment. Compared with other herbicides and growth regulators, the novel compounds of the formula I are effective even when used at very low rates of application.

The compounds of formula I have in addition pronounced growth-regulating, especially growth-inhibiting, properties. The growth of both monocots and dicots is inhibited. Thus, for example, the compounds of formula I selectively inhibit the growth of leguminosae which are frequently planted as cover crops in tropical regions, so that, while soil erosion between cultivated plants is prevented, the cover crops cannot compete with the cultivated plants.

Inhibition of the vegetative growth of many cultivated plants permits more plants to be sown in a crop area, so that a higher yield may be obtained per unit of area. A further mechanism of yield increase using growth regulators reside in the fact that nutrients are able increasingly to promote flower formation and fruiting, whilst vegetative growth is inhibited.

At higher rates of application, all tested plants are so severely damaged in their development that they die.

The invention also relates to herbicidal and growth-regulating compositions which contain a novel compound of the formula I, and also to methods of controlling weeds pre- and postemergence and of inhibiting the growth of monocots and dicots, especially grasses, tropical cover crops and tobacco plant suckers.

The compounds of the formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation, and are therefore formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulation in e.g. polymer substances. As with the nature of the compositions, the methods of applications, such as spraying, atomising, dusting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

The formulations, i.e. the compositions containing the compound (active ingredient) of the formula I and, where appropriate, a solid or liquid adjuvant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredients with extenders, e.g. solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, as well as epoxidised vegetable oils such as epoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders are normally natural mineral fillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order to improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite; and suitable nonsorbent carriers are materials such as calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g. especially dolomite or pulverised plant residues.

Depending on the nature of the compound of the formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts or higher fatty acids (C₁₀ -C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained e.g. from coconut oil or tallow oil. Mention may also be made of fatty acid methyltaurin salts.

More frequently, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts and contain a C₈ -C₂₂ alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Exampls of alkylarylsulfonates are the sodium, calcium or triethylanolamine salts of dodecylbenzene sulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product. Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide, or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediamine propylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan and polyoxyethylene sorbitan trioleate are also suitable non-ionic surfactants.

Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, as further substituents, lower unsubstituted or halogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation are described e.g. in the following publications:

"McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., 1981; H. Stache, "Tensid-Taschenbuch", 2nd Edition, C. Hanser Verlag, Munich & Vienna, 1981; M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-81.

The pesticidal compositions usually contain 0.1 to 95%, preferably 0.1 to 80%, of a compound of the formula I, 1 to 99.9%, of a solid or liquid adjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the following constituents (%=percentage by weight):

    ______________________________________                                         Emulsifiable concentrates                                                      active ingredient:                                                                              1 to 20%, preferably  5 to 10%                                surfactant:      5 to 30%, preferably 10 to 20%                                liquid carrier: 50 to 94%, preferably 70 to 85%                                Dusts                                                                          active ingredient:                                                                              0.1 to 10%, preferably  0.1 to  1%                            solid carrier:  99.9 to 90%, preferably 99.9 to 99%                            Suspension concentrates                                                        active ingredient:                                                                              5 to 75%, preferably 10 to 50%                                water:          94 to 25%, preferably 90 to 30%                                surfactant:      1 to 40%, preferably  2 to 30%                                Wettable powders                                                               active ingredient:                                                                             0.5 to 90%, preferably  1 to 80%                               surfactant:     0.5 to 20%, preferably  1 to 15%                               solid carrier:    5 to 95%, preferably 15 to 90%                               Granulates                                                                     active ingredient:                                                                              0.5 to 30%, preferably  3 to 15%                              solid carrier:  99.5 to 70%, preferably 97 to 85%.                             ______________________________________                                    

Whereas commercial products will be preferably formulated as concentrates, the end user will normally employ dilute formulations. The formulations can be diluted to a concentration as low as 0.001% The rates of application are normally from 0.01 to 10 kg a.i./ha, preferably from 0.025 to 5 kg a.i./ha.

The compositions may also contain further ingredients such as stabilisers, antifoams, viscosity regulators, binders, tackifiers, as well as fertilisers and other compounds for obtaining special effects.

The invention is illustrated by the following Examples.

EXAMPLE 1 Preparation of 2-[(4-chlorophenylthio)methylamino]-4-methoxy-6-methylpyrimidine (intermediate) ##STR25##

A mixture of 13.99 g of 2-amino-4-methoxy-6-methylpyrimidine (0.1 mole), 14.8 g of 4-chlorothiophenol (0.1 mole), 9.4 g of aqueous 35% formaldehyde (0.11 mole) and 1 g of acetic acid are heated under reflux for 1 hour in 100 ml of methanol. The resultant solution is clarified by filtration, diluted with 150 ml of toluene and then the solvent is removed in a rotary evaporator. The residue crystallises after standing for some time. The melting point is 78°-82° after recrystallisation from hexane. The yield is 24 g (81% of theory).

The following compounds are prepared in accordance with this Example:

                                      TABLE 1                                      __________________________________________________________________________      ##STR26##                             (IIIa)                                  No.                                                                               R.sup.3                                                                            R.sup.4                                                                               R.sup.5                                                                               E  R.sup.8    m.p. (°C.)                           __________________________________________________________________________     1.01                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH 4-chlorophenyl                                                                            110-113°                             1.02                                                                              OCH.sub.3                                                                          CH.sub.3                                                                              H      CH 4-chlorophenyl                                                                             78-82°                              1.03                                                                              Cl  OCH.sub.3                                                                             H      CH 4-chlorophenyl                                                                            102-105°                             1.04                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                             H      CH 4-chlorophenyl                                                                            112-114°                             1.05                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH 4-fluorophenyl                                                                             96-98°                              1.06                                                                              OCH.sub.3                                                                          CH.sub.3                                                                              H      CH 2,4,5-trichlorophenyl                                                                     117-119°                             1.07                                                                              OCH.sub.3                                                                          CH.sub.3                                                                              H      CH 4-acetylaminophenyl                                                                       182-183°                             1.08                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH β-naphthyl                                                                           115-118°                             1.09                                                                              OCH.sub.3                                                                          CH.sub.3                                                                              H      CH β-naphthyl                                                                           101-102°                             1.10                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH carbanilidomethyl                                                                         128-130°                             1.11                                                                              Cl  OCH.sub.3                                                                             H      CH p-tolyl    106-109°                             1.12                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH CH.sub.2COOH                                                                              123-125° (dec.)                      1.13                                                                              CH.sub.3                                                                           OCH.sub.3                                                                             H      CH CH.sub.2COOH                                                                              160-164°                             1.14                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH CH(CH.sub.3)COOH                                                                          141-145°                             1.15                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH CH.sub.2 CH.sub.2COOH                                                                     150-153°                             1.16                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH CH.sub.2COOCH.sub.3                                                                        71-73°                              1.17                                                                              CH.sub.3                                                                           OCH.sub.3                                                                             H      CH CH.sub.2COOCH.sub.3                                                                        85-87°                              1.18                                                                              CH.sub.3                                                                           OCH.sub.3                                                                             H      CH N-phenylcarbamoyl-                                                                        161-163°                                                     methyl                                                 1.19                                                                              OCH.sub.3                                                                          OCH.sub.3                                                                             H      CH 4-tolyl     84-91°                              1.20                                                                              OCH.sub.3                                                                          CH.sub.2OCH.sub.3                                                                     H      CH 2,4,5-trichlorophenyl                                                                     124-126°                             1.21                                                                              CH.sub.3                                                                           CH.sub.3                                                                              CH.sub.3                                                                              CH 2-carboxylphenyl                                                                          162-163°                             1.22                                                                              CH.sub.3                                                                           CH.sub.3                                                                              C.sub.3 H.sub.7 (i)                                                                   CH 2-carboxylphenyl                                                                          138-141°                             1.23                                                                              CH.sub.3                                                                           CH.sub.3                                                                              CH.sub.2Cl                                                                            CH 2-carboxylphenyl                                                                          220-222°                                                                (dec.)                                      1.24                                                                              CH.sub.3                                                                           CH.sub.3                                                                              COOH   CH 2-carboxylphenyl                                                                          180-182°                                                                (dec.)                                      1.25                                                                              CH.sub.3                                                                           CH.sub.3                                                                              2-Furyl                                                                               CH 2-carboxylphenyl                                                                          169-171°                                                                (dec.)                                      1.26                                                                              CH.sub.3                                                                           CH.sub.3                                                                              4-Chlor-                                                                              CH 2-carboxylphenyl                                                                          193-195°                                           phenyl               (dec.)                                      1.27                                                                              CH.sub.3                                                                           CH.sub.3                                                                              H      CH 2-carboxylphenyl                                                                          226-228°                                                                (dec.)                                      __________________________________________________________________________

EXAMPLE 2 Preparation of 4-dimethylamino-6-methoxy-2-(4-tolylsulfonyl)methylamino-1,3,5-triazine ##STR27##

8.5 g (0.05 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine and 9.1 g (0.05 mole) of toluene-4-sulfinic acid, sodium salt, are suspended in 100 ml of methanol and to the stirred suspension are added, in succession, 4.8 g (0.05 mole) of methanesulfonic acid and 4.7 g (0.055 mole) of aqueous 35% formaldehyde. The batch is then stirred for 30 minutes at room temperature and then for another 90 minutes under reflux. After cooling, the mixture is diluted with 1 liter of water and the crystalline precipitate is filtered with suction and dried. Melting point: 188°-190° C. Yield: 10 g (59% of theory).

EXAMPLE 3 Preparation of 4,6-dimethyl-2-(4-tolylsulfonylmethylamino)pyrimidine ##STR28##

12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine are suspended in 200 ml of water and then 9.7 g (0.1 mole) of methanesulfonic acid are stirred in to form a solution. To the stirred solution are added, in succession, 18.22 g (0.1 mole) of toluene-3-sulfonic acid, sodium salt, and 9.4 g (0.11 mole) of aqueous 35% formaldehyde. The mixture is stirred for 2 hours at room temperature and for another 30 minute at 90° C. The colourless precipitate is filtered with suction after cooling and dried. Melting point: 191°-194° C. Yield: 25 g (86% of theory).

The following compounds are obtained in accordance with Examples 2 and 3:

                                      TABLE 2                                      __________________________________________________________________________      ##STR29##                         (IIIc)                                      No.                                                                               R.sup.3                                                                             R.sup.4                                                                              R.sup.5                                                                            m E  R.sup.9 m.p. (°C.)                               __________________________________________________________________________     2.01                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H   2 CH CH.sub.3                                                                               145-148                                         2.02                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H   2 CH p-tolyl 191-194°                                 2.03                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             H   2 CH p-tolyl 136-138°                                 2.04                                                                              OCHF.sub.2                                                                          CH.sub.3                                                                             H   2 CH p-tolyl 165-166°                                 2.05                                                                              N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                            H   2 N  p-tolyl 188-190°                                 2.06                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH p-tolyl 135-140°                                 2.07                                                                              OCH.sub.3                                                                           CH.sub.2 COH.sub.3                                                                   H   2 CH p-tolyl 142-144°                                 2.08                                                                              Cl   OCH.sub.3                                                                            H   2 CH p-tolyl                                                 2.09                                                                              Cl   CH.sub.3                                                                             H   2 CH p-tolyl                                                 2.10                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H   2 CH 4-chlorophenyl                                                                         178-180°                                 2.11                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             H   2 CH 4-chlorophenyl                                          2.12                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H   2 CH 4-bromophenyl                                                                          184-186°                                 2.13                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            H   2 CH CH.sub.3                                                                               149-150°                                 2.14                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H   2 CH benzyl  154-159°                                 2.15                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            H   2 CH β-naphthyl                                                                        167-169°                                 2.16                                                                              CH.sub.3                                                                            CH.sub.3                                                                             CH.sub.3                                                                           2 CH p-tolyl 125-127°                                 2.17                                                                              CH.sub.3                                                                            CH.sub.3                                                                             C.sub.3 H.sub.7 i                                                                  2 CH p-tolyl 116-118°                                 2.18                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH CH.sub.3                                                                               149-151°                                 2.19                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH C.sub.2 H.sub.5                                                                        145-147°                                 2.20                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH n-C.sub.3 H.sub.7                                                                      117-120°                                 2.21                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH benzyl  138-139°                                 2.22                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH 2-methoxy-                                                                             135-136°                                                        carbonylbenzyl                                          2.23                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH phenyl  135-139°                                 2.24                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH 2-difluoro-                                                                            137-138°                                                        methoxyphenyl                                           2.25                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH 2,4,6-tri-                                                                             131-133°                                                        methylphenyl                                            2.26                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH 4-bromophenyl                                                                          137-138°                                 2.27                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH 4-chlorophenyl                                                                         140-141°                                 2.28                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H   2 CH β-naphthyl                                                                        139-140°                                 2.29                                                                              OCHF.sub.2                                                                          CH.sub.3                                                                             H   2 CH CH.sub.3                                                                               162-163° (dec.)                          2.30                                                                              N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                            H   2 CH CH.sub.3                                                                               184-187° (dec.)                          __________________________________________________________________________

EXAMPLE 4 Preparation of 4,6-dimethyl-2-(morpholin-4-ylthiocarbonylthiomethylamino)pyrimidine ##STR30##

6.6 g (0.1 mole) of 85% potassium hydroxide and 8.9 g (0.1 mole) of morpholine are dissolved in 200 ml of water and, with cooling, 7.7 g (0.1 mole) of carbon disulfide are added. The mixture is stirred until a yellowish homogeneous solution is obtained. With cooling and stirring, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and a solution of 12.7 g (0.1 mole) of 2-amino-4,6-dimethylpyrimidine and 9.7 g (0.1 mole) of methanesulfonic acid in 50 ml of water are added in succession. The reaction mixture is further stirred at room temperature, whereupon first an oil precipitates, which crystallises after a short time. After 24 hours the batch is diluted with 1 liter of water and the crystalline precipitate is filtered with suction and dried, affording 24 g (80% of theory) of the title compound with a melting point of 119°-121° C.

The following compounds are prepared in accordance with Example 4:

                  TABLE 3                                                          ______________________________________                                          ##STR31##                                                                                                              m.p.                                  No.  R.sup.3  R.sup.4 E    R.sup.9       (°C.)                          ______________________________________                                         3.01 CH.sub.3 CH.sub.3                                                                               CH   pyrrolidinothiocarbonyl                                                                      116-                                                                           118°                           3.02 CH.sub.3 CH.sub.3                                                                               CH   morpholinothiocarbonyl                                                                       119-                                                                           121°                           3.03 Cl       OCH.sub.3                                                                              CH   pyrrolidinothiocarbonyl                                                                      136-                                                                           139°                           3.04 CH.sub.3 CH.sub.3                                                                               CH   azepinylthiocarbonyl                                                                          90- 92°                       3.05 CH.sub.3 CH.sub.3                                                                               CH   methoxythiocarbonyl                                 3.06 CH.sub.3 CH.sub.3                                                                               CH   dimethylthiocarbamoyl                                                                        105-                                                                           115°                           3.07 CH.sub.3 CH.sub.3                                                                               CH   acetyl                                              3.08 CH.sub.3 CH.sub.3                                                                               CH   benzoyl       >110°                                                                   (dec.)                                3.09 OCHF.sub.2                                                                              CH.sub.3                                                                               CH   benzoyl       125-                                                                           128°                                                                    (dec.)                                3.10 CH.sub.3 OCH.sub.3                                                                              CH   benzoyl       107-                                                                           109°                           ______________________________________                                    

EXAMPLE 5 Preparation of 4-methoxy-6-methyl-2-(1,2,4-triazol-1-ylmethylamino)pyrimidine ##STR32##

With stirring, a mixture of 13.9 g (0.1 mole) of 2-amino-4-methoxy-6-methylpyrimidine, 7 g (0.1 mole) of 1,2,4-triazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of methanol is refluxed for 11/2 hours. First a clear solution forms, from which the reaction product precipitates in crystalline form after a time. After the reaction mixture has cooled, the crystalline title compound is filtered with suction and dried. Yield: 14 g. Melting point: 191°-193° C.

EXAMPLE 6 Preparation of 2-[(2,6-dichlorophenyl)-(1,2,4-triazol-1-yl)methyl]-amino-4,6-dimethylpyrimidine ##STR33##

With stirring, a mixture of 6.3 g (0.05 mole) of 2-amino-4,6-dimethylpyrimidine, 8.8 g (0.05 mole) of 2,6-dichlorobenzaldehyde, 3.5 g (0.105 mole) of 1,2,4-triazole and 1 g of acetic acid in 50 ml of methanol is heated under reflux for 2 hours. The resultant clear yellowish solution is concentrated in a rotary evaporator and the residue is crystallised from methanol, affording 6 g (34% of theory) of the title compound, which undergoes conversion at 140°-145° C. and then melts at 158°-159° C.

EXAMPLE 7 Preparation of 2-(benztriazol-1-ylmethylamino)-4-dimethylamino-6-methoxy-1,3,5-triazine ##STR34##

With stirring, a mixture of 16.9 g (0.1 mole) of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine, 12 g (0.1 mole) of benztriazole, 9.4 g (0.11 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 100 ml of ethanol is heated under reflux for 2 hours. The still hot solution is clarified by filtration and crystals of the title compound precipitate from the cooled solution. The precipitate is filtered with suction and dried, affording 25 g (83% of theory) of crystalline product with a melting point of 222°-224° C.

EXAMPLE 8 Preparation of 4,6-dimethyl-2-[2-methylbenzimidizol-1-yl)methylamino]pyrimidine ##STR35##

With stirring, a mixture of 6.3 g (0.05 mole) of 2-amino-4,6-di-methylpyrimidne, 6.7 g (0.05 mole), 4.7 g (0.0055 mole) of aqueous 35% formaldehyde and 1 g of acetic acid in 50 ml of methanol is heated under reflux for 11/2 hours. To the resultant colourless solution are added 150 ml of toluene and the solvent is then removed in a rotary evaporator. The precipitated crystalline residue is recrystallised from ethyl acetete/methanol, affording 10 g (70% of theory) of the title compound which melts at 207°-212° C.

The following compounds are obtained by procedures analogous to those described in Examples 5 to 8:

                                      TABLE 4                                      __________________________________________________________________________      ##STR36##                                                                     __________________________________________________________________________     No.                                                                               R.sup.3                                                                             R.sup.4                                                                              R.sup.5                                                                           E  R.sup.9    m.p. (°C.)                               __________________________________________________________________________     4.01                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH 1,2,4-triazol 1-yl                                                                        162-164°                                 4.02                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             H  CH 1,2,4-triazol-1-yl                                                                        191-193°                                 4.03                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H  CH 1,2,4-triazol-1-yl                                                                        166-168°                                 4.04                                                                              OCHF.sub.2                                                                          CH.sub.3                                                                             H  CH 1,2,4-triazol-1-yl                                                                        187-189°                                 4.05                                                                              OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                   H  CH 1,2,4-triazol-1-yl                                                                        180-181°                                 4.06                                                                              Cl   OCH.sub.3                                                                            H  CH 1,2,4-triazol-1-yl                                                                        157-159°                                 4.07                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H  N  1,2,4-triazol-1-yl                                                                        197-200°                                                                (dec.)                                          4.08                                                                              N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                            H  N  1,2,4-triazol-1-yl                                                                        206-208°                                 4.09                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH benztriazol-1-yl                                                                          204-205°                                 4.10                                                                              OCH.sub.3                                                                           CH.sub.3                                                                             H  CH benztriazol-1-yl                                                                          165-167°                                 4.11                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H  CH benztriazol-1-yl                                                                          168-170°                                 4.12                                                                              OCH.sub.3                                                                           CH.sub.2 OCH.sub.3                                                                   H  CH benztriazol-1-yl                                                                          132-134°                                 4.13                                                                              OCHF.sub.2                                                                          CH.sub.3                                                                             H  CH benztriazol-1-yl                                                                          142-144°                                 __________________________________________________________________________     No.                                                                               R.sup.3                                                                             R.sup.4                                                                              R.sup.5                                                                           E  R.sup.8    m.p. (°C.)                               __________________________________________________________________________     4.14                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            H  CH 5(6)-nitro-benz-                                                                          190-193°*                                                    triazol-1-yl                                               4.15                                                                              OCH.sub.3                                                                           OCH.sub.3                                                                            H  CH 5(6)-nitro-benz-                                                                          173-175°*                                                    triazol-1-yl                                               4.16                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            H  CH 5(6)-chlorobenz-                                                                          156-168°*                                                    triazol-1-yl                                               4.17                                                                              N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                            H  N  benztriazol-1-yl                                                                          222-224°                                 4.18                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH 4aH-carbazol-1-yl                                                                         153-155°                                 4.19                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH 2-methyl-benz-                                                                            207-212°                                                     imidazol-1-yl                                              4.20                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH 2,3-dimethylindol-1-yl                                     4.21                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            H  N  2,3-dimethylindol-1-yl                                     4.22                                                                              OCHF.sub.2                                                                          CH.sub.3                                                                             H  CH 2,3-dimethylindol-1-yl                                     4.23                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH 2,4,5-tribromimidazol-1-yl                                 4.24                                                                              CH.sub.3                                                                            CH.sub.3                                                                             H  CH 2,4,5-tribromimidazol-1-yl                                 4.25                                                                              N(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                            H  N  2,4,5-tribromimidazol-1-yl                                 4.26                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            H  CH pyrazol-1-yl                                               4.27                                                                              OCHF.sub.2                                                                          CH.sub.3                                                                             H  CH pyrazol-1-yl                                               4.28                                                                              Cl   OCH.sub.3                                                                            H  N  pyrazol-1-yl                                               4.29                                                                              CH.sub.3                                                                            OCH.sub.3                                                                            CH.sub.3                                                                          CH 1,2,4-triazol-1-yl                                         __________________________________________________________________________      *mixture of isomers                                                      

EXAMPLE 9 Preparation of N-2-chlorophenylsulfonyl-N'-(4-chlorophenylthiomethyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea ##STR37##

7.5 g (0.027 mole) of 2-(4-chlorophenylthio)methylamino-4,6-dimethylpyrimidine are suspended in 50 ml of absolute acetonitrile and then 5.8 g (0.027 mole) of 2-chlorophenylisocyanate are added. The batch is stirred for 24 hours at room temperature, then the solvent is removed in a rotary evaporator and the residue is taken up in ethyl acetate. The solution is purified by chromatography through a column of silica gel eluted with ethyl acetetate/cyclohexane. The title compound precipitates in crystalline form after removal of the solvent by evaporation. Yield: 6.0 g (45% of theory). Melting point: 132°-135° C.

EXAMPLE 10 Preparation of N-(2-difluoromethoxyphenylsulfonyl)-N'-(p-tolylulfonylmethyl)-N'-(-4-difluorom ethoxy-6-methylpyrimidin-2-yl)urea ##STR38##

5.5 g (0.016 mole) of 4-difluoromethoxy-6-methyl-2-p-tolylsulfonylmethylaminopyrimidine are suspended in 50 ml of absolute dioxan and then 4 g (0.016 mole) of 2-difluoromethoxyphenylisocyanate are stirred into the suspension. Stirring is continued for 3 hours at room temperature to give a clear solution, which is concentrated in a rotary evaporator. The residue crystallises spontaneously when stirred in ether. The crystals are filtered with suction and dried, affording 8 g (84% of theory) of crystalline title compound with a melting point of 159°-164° C. (dec.).

EXAMPLE 11 Preparation of N-(2-chlorophenylsulfonyl)-N'-(pyrrolidinothiocarbonylthiomethyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea ##STR39##

5.5 g (0.019 mole) of 2-(pyrrolidinothiocarbonylthiomethyl)-4,6-dimethylpyrimidine are suspended in 30 ml of absolute acetonitrile and then 4.3 g (0.019 mole) of 2-chlorophenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 5 hours at room temperature to give first a clear solution from which the final product precipitates after a time. The reaction mixture is cooled and then filtered with suction, affording 6 g (63% of theory) of title compound which melts at 131°-133° C. with decomposition.

EXAMPLE 12 Preparation of N-(2-chlorophenylsulfonyl)-N'-(1,2,4-triazol-1-ylmethyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea ##STR40##

4 g (0.019 mole) of 2-(1,2,4-triazol-1-ylmethylamino)-4,6-dimethylpyrimidine are suspended in 100 ml of absolute acetonitrile and then 4.3 g (0.019 mole) of 2-chlorophenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 24 hours at room temperature and the resultant solution is finally concentrated in a rotary evaporator. Crystals of the title compound precipitate and are recrystallised from ethyl acetate, affording 5 g (62% of theory) of the above urea, which melts at 152°-157° C.

EXAMPLE 13 Preparation of N-(2-(2-methoxycarbonylphenylsulfonyl-N'-(benztriazol-1-methyl)-N'-4,6-dimethylpyrimidin-2-yl)urea ##STR41##

6.5 g (0.026 mole) of 2-(benztriazol-1-ylmethylaminop)-4,6-dimethylpyrimidine are suspended in 70 ml of absolute dioxan and then 6.2 g (0.026 mole) of 2-methoxycarbonylphenylsulfonylisocyanate are stirred into the suspension. The batch is stirred for 24 hours at room temperature and the resultant solution is concentrated in a rotary evaporator. The residue is taken up in ethyl acetate and the solution is purified by chromatography through a column of silica gel eluted with ethyl acetate/cyclohexane. The solvent is evaporated off, affording 7.5 g (58% of theory) of crystalline title compound with a melting point of 178°-180° C. (dec.).

The following compounds are prepared by procedures analogous to those described in Examples 9-13:

                                      TABLE 5                                      __________________________________________________________________________      ##STR42##                                                                     No R.sup.1                                                                               R.sup.5                                                                             m R.sup.9     E  m.p. (°C.)                              __________________________________________________________________________     5.001                                                                             COOCH.sub.3                                                                           H    2 p-tolyl     CH 159-160°                                5.002                                                                             COOCH.sub.3                                                                           H    0 p-tolyl     CH                                                5.003                                                                             COOCH.sub.3                                                                           H    2 4-chlorophenyl                                                                             CH                                                5.004                                                                             COOCH.sub.3                                                                           H    0 4-chlorophenyl                                                                             CH 141-144°                                5.005                                                                             COOCH.sub.3                                                                           H    0 acetyl      CH                                                5.006                                                                             COOCH.sub.3                                                                           H    0 benzoyl     CH                                                5.007                                                                             COOCH.sub.3                                                                           H    2 CH.sub.3    CH 130-135° (dec.)                         5.008                                                                             COOCH.sub.3                                                                           H    2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH                                                5.009                                                                             COOCH.sub.3                                                                           H    2 CH(CH.sub.3).sub.2                                                                         CH                                                5.010                                                                             COOCH.sub.3                                                                           H    2 benzyl      CH                                                5.011                                                                             COOCH.sub.3                                                                           H    2 phenyl      CH                                                5.012                                                                             COOCH.sub.3                                                                           H    0 phenyl      CH                                                5.013                                                                             COOCH.sub.3                                                                           H    2 4-bromophenyl                                                                              CH                                                5.014                                                                             COOCH.sub.3                                                                           H    0 4-bromophenyl                                                                              CH                                                5.015                                                                             COOCH.sub.3                                                                           H    2 2-chlorophenyl                                                                             CH                                                5.016                                                                             COOCH.sub.3                                                                           H    0 2-chlorophenyl                                                                             CH                                                5.017                                                                             COOCH.sub.3                                                                           H    0 CH.sub.3    CH                                                5.018                                                                             COOCH.sub.3                                                                           H    0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH                                                5.019                                                                             COOCH.sub.3                                                                           H    0 CH(CH.sub.3).sub.2                                                                         CH                                                5.020                                                                             COOCH.sub.3                                                                           H    0 benzyl      CH                                                5.021                                                                             COOCH.sub.3                                                                           H    2 β-naphthyl                                                                            CH                                                5.022                                                                             COOCH.sub.3                                                                           H    0 β-naphthyl                                                                            CH 178-183° (dec.)                         5.023                                                                             COOCH.sub.3                                                                           H    2 1,2,4-trichloro-                                                                           CH                                                                 phenyl                                                        5.024                                                                             COOCH.sub.3                                                                           H    0 1,2,4-trichloro-                                                                           CH                                                                 phenyl                                                        5.025                                                                             COOCH.sub.3                                                                           H    2 α-naphthyl                                                                           CH                                                5.026                                                                             COOCH.sub.3                                                                           H    2 α-naphthyl                                                                           CH                                                5.027                                                                             COOCH.sub.3                                                                           H    0 CH.sub.2 COOCH.sub.3                                                                       CH                                                5.028                                                                             COOCH.sub.3                                                                           H    2 4-fluorophenyl                                                                             CH                                                5.029                                                                             COOCH.sub.3                                                                           H    0 4-fluorophenyl                                                                             CH                                                5.030                                                                             COOCH.sub.3                                                                           H    0 4-nitrophenyl                                                                              CH                                                5.031                                                                             COOCH.sub.3                                                                           H    0 4-nitrophenyl                                                                              CH                                                5.032                                                                             COOCH.sub.3                                                                           H    2 2-nitrophenyl                                                                              CH                                                5.033                                                                             COOCH.sub.3                                                                           H    0 2-nitrophenyl                                                                              CH                                                5.034                                                                             COOCH.sub.3                                                                           H    2 2-trifluoromethyl                                                                          CH                                                5.035                                                                             COOCH.sub.3                                                                           H    0 2-trifluoromethyl                                                                          CH                                                5.036                                                                             COOCH.sub.3                                                                           H    2 4-methoxyphenyl                                                                            CH                                                5.037                                                                             COOCH.sub.3                                                                           H    0 4-methoxyphenyl                                                                            CH                                                5.038                                                                             COOCH.sub.3                                                                           H    2 2-methoxyphenyl                                                                            CH                                                5.039                                                                             COOCH.sub.3                                                                           H    0 2-methoxyphenyl                                                                            CH                                                5.040                                                                             COOCH.sub.3                                                                           H    2 2,4,6-trimethyl-                                                                           CH                                                                 phenyl                                                        5.041                                                                             COOCH.sub.3                                                                           H    0 2,4,6-trimethyl-                                                                           CH                                                                 phenyl                                                        5.042                                                                             COOCH.sub.3                                                                           H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.043                                                                             COOCH.sub.3                                                                           H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                               CH                                                5.044                                                                             COOCH.sub.3                                                                           H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                               CH                                                5.045                                                                             COOCH.sub.3                                                                           H    0 pyrrolidinothio-                                                                           CH                                                                 carbonyl                                                      5.046                                                                             COOCH.sub.3                                                                           H    0 piperidinothio-                                                                            CH                                                                 carbonyl                                                      5.047                                                                             COOCH.sub.3                                                                           H    0 anilidoacetyl                                                                              CH                                                5.048                                                                             COOCH.sub.3                                                                           H    0 2,4-dichlorophenyl                                                                         CH                                                5.049                                                                             COOCH.sub.3                                                                           H    2 2,4-dichlorophenyl                                                                         CH                                                5.050                                                                             COOCH.sub.3                                                                           H    0 CH.sub.2 COOH                                                                              CH                                                5.051                                                                             COOCH.sub.3                                                                           H    0 CH.sub.2 COO CH.sub.3                                                                      CH 154-156°                                5.052                                                                             COOCH.sub.3                                                                           H    0 CH.sub.2 CON(CH.sub.3).sub.2                                                               CH                                                5.053                                                                             COOCH.sub.3                                                                           H    0 4-chlorophenyl                                                                             N                                                 5.054                                                                             COOCH.sub.3                                                                           H    0 p-tolyl     N                                                 5.055                                                                             COOCH.sub.3                                                                           furyl-2-                                                                            0 2-hydroxy-  CH                                                                 carbonylphenyl                                                5.056                                                                             COOCH.sub.3                                                                           furyl-2-                                                                            0 2-methoxy-  CH                                                                 carbonylphenyl                                                5.057                                                                             COOCH.sub.3                                                                           furyl-2-                                                                            0 phenyl      CH                                                5.058                                                                             COOCH.sub.3                                                                           4-chloro-                                                                           0 2-hydroxy-  CH                                                          phenyl carbonylphenyl                                                5.059                                                                             COOCH.sub.3                                                                           4-chloro-                                                                           0 phenyl      CH                                                          phenyl                                                               5.060                                                                             COOCH.sub.3                                                                           CH.sub.3                                                                            0 4-chlorophenyl                                                                             CH                                                5.061                                                                             OCHF.sub.2                                                                            H    2 p-tolyl     CH 152-157° (dec.)                         5.062                                                                             OCHF.sub.2                                                                            H    0 p-tolyl     CH                                                5.063                                                                             OCHF.sub.2                                                                            H    2 4-chlorophenyl                                                                             CH                                                5.064                                                                             OCHF.sub.2                                                                            H    0 4-chlorophenyl                                                                             CH 109-111°                                5.065                                                                             OCHF.sub.2                                                                            H    0 acetyl      CH                                                5.066                                                                             OCHF.sub.2                                                                            H    0 benzoyl     CH 155-158°                                                                dec.                                           5.067                                                                             OCHF.sub.2                                                                            H    2 CH.sub.3    CH                                                5.068                                                                             OCHF.sub.2                                                                            H    2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH                                                5.069                                                                             OCHF.sub.2                                                                            H    2 CH(CH.sub.3).sub.2                                                                         CH                                                5.070                                                                             OCHF.sub.2                                                                            H    2 benzyl      CH                                                5.071                                                                             OCHF.sub.2                                                                            H    2 phenyl      CH                                                5.072                                                                             OCHF.sub.2                                                                            H    0 phenyl      CH                                                5.073                                                                             OCHF.sub.2                                                                            H    2 4-bromophenyl                                                                              CH                                                5.074                                                                             OCHF.sub.2                                                                            H    0 4-bromophenyl                                                                              CH                                                5.075                                                                             OCHF.sub.2                                                                            H    2 2-chlorophenyl                                                                             CH                                                5.076                                                                             OCHF.sub.2                                                                            H    0 2-chlorophenyl                                                                             CH                                                5.077                                                                             OCHF.sub.2                                                                            H    0 CH.sub.3    CH                                                5.078                                                                             OCHF.sub.2                                                                            H    0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH                                                5.079                                                                             OCHF.sub.2                                                                            H    0 CH(CH.sub.3).sub.2                                                                         CH                                                5.080                                                                             OCHF.sub.2                                                                            H    0 benzyl      CH                                                5.081                                                                             OCHF.sub.2                                                                            H    2 β-naphthyl                                                                            CH                                                5.082                                                                             OCHF.sub.2                                                                            H    0 β-naphthyl                                                                            CH 162-164°                                5.083                                                                             OCHF.sub.2                                                                            H    2 1,2,4-trichloro-                                                                           CH                                                                 phenyl                                                        5.084                                                                             OCHF.sub.2                                                                            H    0 1,2,4-trichloro-                                                                           CH                                                                 phenyl                                                        5.085                                                                             OCHF.sub.2                                                                            H    2 α-naphthyl                                                                           CH                                                5.086                                                                             OCHF.sub.2                                                                            H    2 α-naphthyl                                                                           CH                                                5.087                                                                             OCHF.sub.2                                                                            H    0 CH.sub.2 COOCH.sub.3                                                                       CH                                                5.088                                                                             OCHF.sub.2                                                                            H    2 4-fluorophenyl                                                                             CH                                                5.089                                                                             OCHF.sub.2                                                                            H    0 4-fluorophenyl                                                                             CH 125-127°                                5.090                                                                             OCHF.sub.2                                                                            H    0 4-nitrophenyl                                                                              CH                                                5.091                                                                             OCHF.sub.2                                                                            H    0 4-nitrophenyl                                                                              CH                                                5.092                                                                             OCHF.sub.2                                                                            H    2 2-nitrophenyl                                                                              CH                                                5.093                                                                             OCHF.sub.2                                                                            H    0 2-nitrophenyl                                                                              CH                                                5.094                                                                             OCHF.sub.2                                                                            H    2 2-trifluoromethyl                                                                          CH                                                5.095                                                                             OCHF.sub.2                                                                            H    0 2-trifluoromethyl                                                                          CH                                                5.096                                                                             OCHF.sub.2                                                                            H    2 4-methoxyphenyl                                                                            CH                                                5.097                                                                             OCHF.sub.2                                                                            H    0 4-methoxyphenyl                                                                            CH                                                5.098                                                                             OCHF.sub.2                                                                            H    2 2-methoxyphenyl                                                                            CH                                                5.099                                                                             OCHF.sub.2                                                                            H    0 2-methoxyphenyl                                                                            CH                                                5.100                                                                             OCHF.sub.2                                                                            H    2 2,4,6-trimethyl-                                                                           CH                                                                 phenyl                                                        5.101                                                                             OCHF.sub.2                                                                            H    0 2,4,6-trimethyl-                                                                           CH                                                                 phenyl                                                        5.102                                                                             OCHF.sub.2                                                                            H    0 CSN(CH.sub.3).sub.2                                                                        CH 139-142°                                                                dec.                                           5.103                                                                             OCHF.sub.2                                                                            H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                               CH                                                5.104                                                                             OCHF.sub.2                                                                            H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                               CH                                                5.105                                                                             OCHF.sub.2                                                                            H    0 pyrrolidinothio-                                                                           CH 136-139°                                                 carbonyl       dec.                                           5.106                                                                             OCHF.sub.2                                                                            H    0 piperidinothio-                                                                            CH                                                                 carbonyl                                                      5.107                                                                             OCHF.sub.2                                                                            H    0 N-phenylcarbamoyl-                                                                         CH 110-112°                                                 methyl                                                        5.108                                                                             OCHF.sub.2                                                                            H    0 2,4-dichlorophenyl                                                                         CH                                                5.109                                                                             OCHF.sub.2                                                                            H    2 2,4-dichlorophenyl                                                                         CH                                                5.110                                                                             OCHF.sub.2                                                                            H    0 CH.sub.2 COOH                                                                              CH                                                5.111                                                                             OCHF.sub.2                                                                            H    0 CH.sub.2 COO CH.sub.3                                                                      CH                                                5.112                                                                             OCHF.sub.2                                                                            H    0 CH.sub.2 CON(CH.sub.3).sub.2                                                               CH                                                5.113                                                                             OCHF.sub.2                                                                            H    0 4-chlorophenyl                                                                             N                                                 5.114                                                                             OCHF.sub.2                                                                            H    0 p-tolyl     N                                                 5.115                                                                             OCHF.sub.2                                                                            Furyl-2-                                                                            0 2-hydroxy-  CH                                                                 carbonylphenyl                                                5.116                                                                             OCHF.sub.2                                                                            Furyl-2-                                                                            0 2-methoxy-  CH                                                                 carbonylphenyl                                                5.117                                                                             OCHF.sub.2                                                                            Furyl-2-                                                                            0 phenyl      CH                                                5.118                                                                             OCHF.sub.2                                                                            4-Chlor-                                                                            0 2-hydroxy-  CH                                                          phenyl carbonylphenyl                                                5.119                                                                             OCHF.sub.2                                                                            4-Chlor-                                                                            0 phenyl      CH                                                          phenyl                                                               5.120                                                                             OCHF.sub.2                                                                            CH.sub.3                                                                            0 4-chlorophenyl                                                                             CH                                                5.121                                                                             Cl     H    2 p-tolyl     CH 153-155°                                5.122                                                                             Cl     H    0 p-tolyl     CH 86-88 (dec.)                                   5.123                                                                             Cl     H    2 4-chlorophenyl                                                                             CH                                                5.124                                                                             Cl     H    0 4-chlorophenyl                                                                             CH 132-135°                                                                dec.                                           5.125                                                                             Cl     H    0 acetyl      CH                                                5.126                                                                             Cl     H    0 benzoyl     CH                                                5.127                                                                             Cl     H    2 CH.sub.3    CH                                                5.128                                                                             Cl     H    2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH                                                5.129                                                                             Cl     H    2 CH(CH.sub.3).sub.2                                                                         CH                                                5.130                                                                             Cl     H    2 benzyl      CH 146-147° (dec.)                         5.131                                                                             Cl     H    2 phenyl      CH                                                5.132                                                                             Cl     H    0 phenyl      CH                                                5.133                                                                             Cl     H    2 4-bromophenyl                                                                              CH 150-153° (dec.)                         5.134                                                                             Cl     H    0 4-bromophenyl                                                                              CH                                                5.135                                                                             Cl     H    2 2-chlorophenyl                                                                             CH                                                5.136                                                                             Cl     H    0 2-chlorophenyl                                                                             CH                                                5.137                                                                             Cl     H    0 CH.sub.3    CH                                                5.138                                                                             Cl     H    0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH                                                5.139                                                                             Cl     H    0 CH(CH.sub.3).sub.2                                                                         CH                                                5.140                                                                             Cl     H    0 benzyl      CH                                                5.141                                                                             Cl     H    2 β-naphthyl                                                                            CH                                                5.142                                                                             Cl     H    0 β-naphthyl                                                                            CH 156-158°                                5.143                                                                             Cl     H    2 1,2,4-trichloro-                                                                           CH                                                                 phenyl                                                        5.144                                                                             Cl     H    0 1,2,4-trichloro-                                                                           CH                                                                 phenyl                                                        5.145                                                                             Cl     H    2 α-naphthyl                                                                           CH                                                5.146                                                                             Cl     H    2 α-naphthyl                                                                           CH                                                5.147                                                                             Cl     H    0 CH.sub.2 COOCH.sub.3                                                                       CH                                                5.148                                                                             Cl     H    2 4-fluorophenyl                                                                             CH                                                5.149                                                                             Cl     H    0 4-fluorophenyl                                                                             CH                                                5.150                                                                             Cl     H    0 4-nitrophenyl                                                                              CH                                                5.151                                                                             Cl     H    0 4-nitrophenyl                                                                              CH                                                5.152                                                                             Cl     H    2 2-nitrophenyl                                                                              CH                                                5.153                                                                             Cl     H    0 2-nitrophenyl                                                                              CH                                                5.154                                                                             Cl     H    2 2-trifluoromethyl                                                                          CH                                                5.155                                                                             Cl     H    0 2-trifluoromethyl                                                                          CH                                                5.156                                                                             Cl     H    2 4-methoxyphenyl                                                                            CH                                                5.157                                                                             Cl     H    0 4-methoxyphenyl                                                                            CH                                                5.158                                                                             Cl     H    2 2-methoxyphenyl                                                                            CH                                                5.159                                                                             Cl     H    0 2-methoxyphenyl                                                                            CH                                                5.160                                                                             Cl     H    2 2,4,6-trimethyl-                                                                           CH                                                                 phenyl                                                        5.161                                                                             Cl     H    0 2,4,6-trimethyl-                                                                           CH                                                                 phenyl                                                        5.162                                                                             Cl     H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.163                                                                             Cl     H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                               CH                                                5.164                                                                             Cl     H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                               CH                                                5.165                                                                             Cl     H    0 pyrrolidinothio-                                                                           CH 131-133°                                                 carbonyl       dec.                                           5.166                                                                             Cl     H    0 piperidinothio-                                                                            CH                                                                 carbonyl                                                      5.167                                                                             Cl     H    0 N-phenylcarbamoyl-                                                                         CH 110-112°                                                 methyl                                                        5.168                                                                             Cl     H    0 2,4-dichlorophenyl                                                                         CH                                                5.169                                                                             Cl     H    2 2,4-dichlorophenyl                                                                         CH                                                5.170                                                                             Cl     H    0 CH.sub.2 COOH                                                                              CH 123-125° (dec.)                         5.171                                                                             Cl     H    0 CH.sub.2 COO CH.sub.3                                                                      CH                                                5.172                                                                             Cl     H    0 CH.sub.2 CON(CH.sub.3).sub.2                                                               CH                                                5.173                                                                             Cl     H    0 4-chlorophenyl                                                                             N                                                 5.174                                                                             Cl     H    0 p-tolyl     N                                                 5.175                                                                             Cl     furyl-2-                                                                            0 2-hydroxy-  CH                                                                 carbonylphenyl                                                5.176                                                                             Cl     furyl-2-                                                                            0 2-methoxy-  CH                                                                 carbonylphenyl                                                5.177                                                                             Cl     furyl-2-                                                                            0 phenyl      CH                                                5.178                                                                             Cl     4-chloro-                                                                           0 2-hydroxy-  CH                                                          phenyl carbonylphenyl                                                5.179                                                                             Cl     4-chloro-                                                                           0 phenyl      CH                                                          phenyl                                                               5.180                                                                             Cl     CH.sub.3                                                                            0 4-chlorophenyl                                                                             CH                                                5.181                                                                             OCH.sub.3                                                                             H    0 phenyl      CH                                                5.182                                                                             OCH.sub.3                                                                             H    2 phenyl      CH                                                5.183                                                                             OCH.sub.3                                                                             H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.184                                                                             OCH.sub.3                                                                             H    0 pyrrolidinothio-                                                                           CH                                                                 carbonyl                                                      5.185                                                                             OCH.sub.3                                                                             H    0 CH.sub.3    CH                                                5.186                                                                             OCH.sub.3                                                                             H    2 CH.sub.3    CH                                                5.187                                                                             NO.sub.2                                                                              H    0 phenyl      CH                                                5.188                                                                             NO.sub.2                                                                              H    2 phenyl      CH                                                5.189                                                                             NO.sub.2                                                                              H    0 CSN(CH.sub. 3).sub.2                                                                       CH                                                5.190                                                                             NO.sub.2                                                                              H    0 pyrrolidinothio-                                                                           CH                                                                 carbonyl                                                      5.191                                                                             NO.sub.2                                                                              H    0 CH.sub.3    CH                                                5.192                                                                             NO.sub.2                                                                              H    2 CH.sub.3    CH                                                5.193                                                                             CF.sub.3                                                                              H    0 phenyl      CH                                                5.194                                                                             CF.sub.3                                                                              H    2 phenyl      CH                                                5.195                                                                             CF.sub.3                                                                              H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.196                                                                             CF.sub.3                                                                              H    0 pyrrolidino-                                                                               CH                                                                 thiocarbonyl                                                  5.197                                                                             CF.sub.3                                                                              H    0 CH.sub.3    CH                                                5.198                                                                             CF.sub.3                                                                              H    2 CH.sub.3    CH                                                5.199                                                                             OSO.sub.2 CH.sub.3                                                                    H    0 phenyl      CH                                                5.200                                                                             OSO.sub.2 CH.sub.3                                                                    H    2 phenyl      CH                                                5.201                                                                             OSO.sub.2 CH.sub.3                                                                    H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.202                                                                             OSO.sub.2 CH.sub.3                                                                    H    0 pyrrolidino-                                                                               CH                                                                 thiocarbonyl                                                  5.203                                                                             OSO.sub.2 CH.sub.3                                                                    H    0 CH.sub.3    CH                                                5.204                                                                             OSO.sub.2 CH.sub.3                                                                    H    2 CH.sub.3    CH                                                5.205                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                           H    2 phenyl      CH                                                5.206                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                           H    2 phenyl      CH                                                5.207                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                           H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.208                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                           H    0 pyrrolidino-                                                                               CH                                                                 thiocarbonyl                                                  5.209                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                           H    2 CH.sub.3    CH                                                5.210                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                           H    0 CH.sub.3    CH                                                5.211                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                            H    0 phenyl      CH                                                5.212                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                            H    2 phenyl      CH                                                5.213                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                            H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.214                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                            H    0 pyrrolidino-                                                                               CH                                                                 thiocarbonyl                                                  5.215                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                            H    0 CH.sub.3    CH                                                5.216                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                            H    2 CH.sub.3    CH                                                5.217                                                                             CH.sub.3                                                                              H    0 phenyl      CH                                                5.218                                                                             CH.sub.3                                                                              H    2 phenyl      CH                                                5.219                                                                             CH.sub.3                                                                              H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.220                                                                             CH.sub.3                                                                              H    0 pyrrolidino-                                                                               CH                                                                 thiocarbonyl                                                  5.221                                                                             CH.sub.3                                                                              H    0 CH.sub.3    CH                                                5.222                                                                             CH.sub.3                                                                              H    2 CH.sub.3    CH                                                5.223                                                                             SO.sub.2 CH.sub.3                                                                     H    0 phenyl      CH                                                5.224                                                                             SO.sub.2 CH.sub.3                                                                     H    2 phenyl      CH                                                5.225                                                                             SO.sub.2 CH.sub.3                                                                     H    0 CSN(CH.sub.3).sub.2                                                                        CH                                                5.226                                                                             SO.sub.2 CH.sub.3                                                                     H    0 pyrrolidino-                                                                               CH                                                                 thiocarbonyl                                                  5.227                                                                             SO.sub.2 CH.sub.3                                                                     H    0 CH.sub.3    CH                                                5.228                                                                             SO.sub.2 CH.sub.3                                                                     H    2 CH.sub.3    CH                                                5.229                                                                             CH.sub.3                                                                              H    2 p-tolyl     CH 148-150°                                                                dec.                                           5.230                                                                             CH.sub.3                                                                              H    0 morpholino- CH 145-146°                                                 thiocarbonyl   dec.                                           5.231                                                                             OCHF.sub.2                                                                            H    0 morpholino- CH 132-134°                                                 thiocarbonyl   dec.                                           5.232                                                                             OCHF.sub.2                                                                            H    0 4-fluorophenyl                                                                             CH 125-127°                                5.233                                                                             COOCH.sub.3                                                                           H    0 4-fluorophenyl                                                                             CH                                                5.234                                                                             COOCH.sub.3                                                                           H    2 4-fluorophenyl                                                                             CH                                                5.235                                                                             CH.sub.3                                                                              H    2 benzyl      CH 146-148°                                                                dec.                                           5.236                                                                             CH.sub.3                                                                              H    2 4-bromophenyl                                                                              CH 141-143°                                                                dec.                                           5.237                                                                             Cl     CH.sub.3                                                                            2 p-tolyl     CH 126-129°                                                                dec.                                           5.238                                                                             Cl     H    0 2-carboxyphenyl                                                                            CH 134-138°                                                                dec.                                           5.239                                                                             2,6-Cl.sub.2                                                                          H    2 benzyl      CH 147-151°                                                                dec.                                           5.240                                                                             2,6-Cl.sub.2                                                                          H    0 β-naphthyl                                                                            CH 149-152°                                5.241                                                                             2,6-Cl.sub.2                                                                          H    2 p-tolyl     CH 163- 166                                                                       dec.                                           5.242                                                                             phenyl H    2 CH.sub.3    CH 162-166°                                                                dec.                                           5.243                                                                             phenyl H    2 p-tolyl     CH 154-157°                                                                dec.                                           5.244                                                                             phenyl H    0 CSN(CH.sub.3).sub.2                                                                        CH 143-145°                                                                dec.                                           5.245                                                                             phenyl H    0 CH.sub.2COOCH.sub.3                                                                        CH 172-174°                                                                dec.                                           5.246                                                                             phenyl H    0 CH.sub.2CH.sub.2COOH                                                                       CH 155-157                                                                        dec.                                           5.247                                                                             phenyl H    0 CH(CH.sub.3)COOH                                                                           CH 150-152°                                                                dec.                                           5.248                                                                             Cl     H    2 phenyl      N                                                 5.249                                                                             Cl     H    2 p-tolyl     N                                                 5.250                                                                             COOCH.sub.3                                                                           H    2 CH.sub.3    N                                                 5.251                                                                             OCHF.sub.2                                                                            H    2 p-tolyl     N                                                 5.252                                                                             NO.sub.2                                                                              H    0 C.sub.2 H.sub.4 COOH                                                                       CH 121-124°                                5.253                                                                             CF.sub.3                                                                              H    0 4-chlorophenyl                                                                             CH 118-121°                                __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________      ##STR43##                                                                     __________________________________________________________________________     No R.sup.1 R.sup.5                                                                             m R.sup.9   E  m.p. (°C.)                               __________________________________________________________________________     6.001                                                                             COOCH.sub.3                                                                            H    2 p-tolyl   CH 148-150° (dec.)                          6.002                                                                             COOCH.sub.3                                                                            H    0 p-tolyl   CH                                                 6.003                                                                             COOCH.sub.3                                                                            H    2 4-chlorophenyl                                                                           CH                                                 6.004                                                                             COOCH.sub.3                                                                            H    0 4-chlorophenyl                                                                           CH                                                 6.005                                                                             COOCH.sub.3                                                                            H    0 acetyl    CH                                                 6.006                                                                             COOCH.sub.3                                                                            H    0 benzoyl   CH                                                 6.007                                                                             COOCH.sub.3                                                                            H    2 CH.sub.3  CH                                                 6.008                                                                             COOCH.sub.3                                                                            H    2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH                                                 6.009                                                                             COOCH.sub.3                                                                            H    2 CH(CH.sub.3).sub.2                                                                       CH                                                 6.010                                                                             COOCH.sub.3                                                                            H    2 benzyl    CH 136-137° (dec.)                          6.011                                                                             COOCH.sub.3                                                                            H    2 phenyl    CH 141- 142° (dec.)                         6.012                                                                             COOCH.sub.3                                                                            H    0 phenyl    CH                                                 6.013                                                                             COOCH.sub.3                                                                            H    2 4-bromophenyl                                                                            CH 134-135° (dec.)                          6.014                                                                             COOCH.sub.3                                                                            H    0 4-bromophenyl                                                                            CH                                                 6.015                                                                             COOCH.sub.3                                                                            H    2 2-chlorophenyl                                                                           CH                                                 6.016                                                                             COOCH.sub.3                                                                            H    0 2-chlorophenyl                                                                           CH                                                 6.017                                                                             COOCH.sub.3                                                                            H    0 CH.sub.3  CH                                                 6.018                                                                             COOCH.sub.3                                                                            H    0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH                                                 6.019                                                                             COOCH.sub.3                                                                            H    0 CH(CH.sub.3).sub.2                                                                       CH                                                 6.020                                                                             COOCH.sub.3                                                                            H    0 benzyl    CH                                                 6.021                                                                             COOCH.sub.3                                                                            H    2 β-naphthyl                                                                          CH 140-141° (dec.)                          6.022                                                                             COOCH.sub.3                                                                            H    0 β-naphtyl                                                                           CH                                                 6.023                                                                             COOCH.sub.3                                                                            H    2 1,2,4-trichloro-                                                                         CH                                                                   phenyl                                                       6.024                                                                             COOCH.sub.3                                                                            H    0 1,2,4-trichloro-                                                                         CH                                                                   phenyl                                                       6.025                                                                             COOCH.sub.3                                                                            H    2 α-naphthyl                                                                         CH                                                 6.026                                                                             COOCH.sub.3                                                                            H    2 α-naphthyl                                                                         CH                                                 6.027                                                                             COOCH.sub.3                                                                            H    0 CH.sub.2 COOCH.sub.3                                                                     CH                                                 6.028                                                                             COOCH.sub.3                                                                            H    2 4-fluorophenyl                                                                           CH                                                 6.029                                                                             COOCH.sub.3                                                                            H    0 4-fluorophenyl                                                                           CH                                                 6.030                                                                             COOCH.sub.3                                                                            H    0 4-nitrophenyl                                                                            CH                                                 6.031                                                                             COOCH.sub.3                                                                            H    0 4-nitrophenyl                                                                            CH                                                 6.032                                                                             COOCH.sub.3                                                                            H    2 2-nitrophenyl                                                                            CH                                                 6.033                                                                             COOCH.sub.3                                                                            H    0 2-nitrophenyl                                                                            CH                                                 6.034                                                                             COOCH.sub.3                                                                            H    2 2-trifluoromethyl-                                                                       CH                                                                   phenyl                                                       6.035                                                                             COOCH.sub.3                                                                            H    0 2-trifluoromethyl-                                                                       CH                                                                   phenyl                                                       6.036                                                                             COOCH.sub.3                                                                            H    2 4-methoxyphenyl                                                                          CH                                                 6.037                                                                             COOCH.sub.3                                                                            H    0 4-methoxyphenyl                                                                          CH                                                 6.038                                                                             COOCH.sub.3                                                                            H    2 2-methoxyphenyl                                                                          CH                                                 6.039                                                                             COOCH.sub.3                                                                            H    0 2-methoxyphenyl                                                                          CH                                                 6.040                                                                             COOCH.sub.3                                                                            H    2 2,4,6-trimethyl-                                                                         CH 133-134° (dec.)                                            phenyl                                                       6.041                                                                             COOCH.sub.3                                                                            H    0 2,4,6-trimethyl-                                                                         CH                                                                   phenyl                                                       6.042                                                                             COOCH.sub.3                                                                            H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.043                                                                             COOCH.sub.3                                                                            H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                             CH 139-140° (dec.)                          6.044                                                                             COOCH.sub.3                                                                            H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                             N                                                  6.045                                                                             COOCH.sub.3                                                                            H    0 pyrrolidinothio-                                                                         CH                                                                   carbonyl                                                     6.046                                                                             COOCH.sub.3                                                                            H    0 piperidinothio-                                                                          CH                                                                   carbonyl                                                     6.047                                                                             COOCH.sub.3                                                                            H    0 N-phenylcarbamoyl-                                                                       CH                                                                   methyl                                                       6.048                                                                             COOCH.sub.3                                                                            H    0 2,4-dichlorophenyl                                                                       CH                                                 6.049                                                                             COOCH.sub.3                                                                            H    2 2,4-dichlorophenyl                                                                       CH                                                 6.050                                                                             COOCH.sub.3                                                                            H    0 CH.sub.2 COOH                                                                            CH                                                 6.051                                                                             COOCH.sub.3                                                                            H    0 CH.sub.2 COOCH.sub. 3                                                                    CH                                                 6.052                                                                             COOCH.sub.3                                                                            H    0 CH.sub.2 CON(CH.sub.3).sub.2                                                             CH                                                 6.053                                                                             COOCH.sub.3                                                                            H    0 4-Chlorophenyl                                                                           N                                                  6.054                                                                             COOCH.sub.3                                                                            H    0 p-tolyl   N                                                  6.055                                                                             COOCH.sub.3                                                                            furyl-2-                                                                            0 2-hydroxy-                                                                               CH                                                                   carbonylphenyl                                               6.056                                                                             COOCH.sub.3                                                                            furyl-2-                                                                            0 2-methoxy-                                                                               CH                                                                   carbonylphenyl                                               6.057                                                                             COOCH.sub.3                                                                            furyl-2-                                                                            0 phenyl    CH                                                 6.058                                                                             COOCH.sub.3                                                                            4-chloro-                                                                           0 2-hydroxy-                                                                               CH                                                            phenyl carbonylphenyl                                               6.059                                                                             COOCH.sub.3                                                                            4-chloro-                                                                           0 phenyl    CH                                                            phenyl                                                              6.060                                                                             COOCH.sub.3                                                                            CH.sub.3                                                                            0 4-chlorophenyl                                                                           CH                                                 6.061                                                                             OCHF.sub.2                                                                             H    2 p-tolyl   CH 142-143°                                 6.062                                                                             OCHF.sub.2                                                                             H    0 p-tolyl   CH                                                 6.063                                                                             OCHF.sub.2                                                                             H    2 4-chlorophenyl                                                                           CH                                                 6.064                                                                             OCHF.sub.2                                                                             H    0 4-chlorophenyl                                                                           CH                                                 6.065                                                                             OCHF.sub.2                                                                             H    0 acetyl    CH                                                 6.066                                                                             OCHF.sub.2                                                                             H    0 benzoyl   CH                                                 6.067                                                                             OCHF.sub.2                                                                             H    2 CH.sub.3 CH                                                  6.068                                                                             OCHF.sub.2                                                                             H    2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH                                                 6.069                                                                             OCHF.sub.2                                                                             H    2 CH(CH.sub.3).sub.2                                                                       CH                                                 6.070                                                                             OCHF.sub.2                                                                             H    2 benzyl    CH                                                 6.071                                                                             OCHF.sub.2                                                                             H    2 phenyl    CH                                                 6.072                                                                             OCHF.sub.2                                                                             H    0 phenyl    CH                                                 6.073                                                                             OCHF.sub.2                                                                             H    2 4-bromophenyl                                                                            CH                                                 6.074                                                                             OCHF.sub.2                                                                             H    0 4-bromophenyl                                                                            CH                                                 6.075                                                                             OCHF.sub.2                                                                             H    2 2-chlorophenyl                                                                           CH                                                 6.076                                                                             OCHF.sub.2                                                                             H    0 2-chlorophenyl                                                                           CH                                                 6.077                                                                             OCHF.sub.2                                                                             H    0 CH.sub.3 CH                                                  6.078                                                                             OCHF.sub.2                                                                             H    0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH                                                 6.079                                                                             OCHF.sub.2                                                                             H    0 CH(CH.sub.3).sub.2                                                                       CH                                                 6.080                                                                             OCHF.sub.2                                                                             H    0 benzyl    CH                                                 6.081                                                                             OCHF.sub.2                                                                             H    2 β-naphthyl                                                                          CH                                                 6.082                                                                             OCHF.sub.2                                                                             H    0 β-naphthyl                                                                          CH                                                 6.083                                                                             OCHF.sub.2                                                                             H    2 1,2,4-trichloro-                                                                         CH                                                                   phenyl                                                       6.084                                                                             OCHF.sub.2                                                                             H    0 1,2,4-trichloro-                                                                         CH                                                                   phenyl                                                       6.085                                                                             OCHF.sub.2                                                                             H    2 α-naphthyl                                                                         CH                                                 6.086                                                                             OCHF.sub.2                                                                             H    2 α-naphthyl                                                                         CH                                                 6.087                                                                             OCHF.sub.2                                                                             H    0 CH.sub.2 COOCH.sub.3                                                                     CH                                                 6.088                                                                             OCHF.sub.2                                                                             H    2 4-fluorophenyl                                                                           CH                                                 6.089                                                                             OCHF.sub.2                                                                             H    0 4-fluorophenyl                                                                           CH                                                 6.090                                                                             OCHF.sub.2                                                                             H    0 4-nitrophenyl                                                                            CH                                                 6.091                                                                             OCHF.sub.2                                                                             H    0 4-nitrophenyl                                                                            CH                                                 6.092                                                                             OCHF.sub.2                                                                             H    2 2-nitrophenyl                                                                            CH                                                 6.093                                                                             OCHF.sub.2                                                                             H    0 2-nitrophenyl                                                                            CH                                                 6.094                                                                             OCHF.sub.2                                                                             H    2 2-trifluoromethyl                                                                        CH                                                 6.095                                                                             OCHF.sub.2                                                                             H    0 2-trifluoromethyl                                                                        CH                                                 6.096                                                                             OCHF.sub.2                                                                             H    2 4-methoxyphenyl                                                                          CH                                                 6.097                                                                             OCHF.sub.2                                                                             H    0 4-methoxyphenyl                                                                          CH                                                 6.098                                                                             OCHF.sub.2                                                                             H    2 2-methoxyphenyl                                                                          CH                                                 6.099                                                                             OCHF.sub.2                                                                             H    0 2-methoxyphenyl                                                                          CH                                                 6.100                                                                             OCHF.sub.2                                                                             H    2 2,4,6-trimethyl-                                                                         CH                                                                   phenyl                                                       6.101                                                                             OCHF.sub. 2                                                                            H    0 2,4,6-trimethyl-                                                                         CH                                                                   phenyl                                                       6.102                                                                             OCHF.sub.2                                                                             H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.103                                                                             OCHF.sub.2                                                                             H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                             CH                                                 6.104                                                                             OCHF.sub.2                                                                             H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                             CH                                                 6.105                                                                             OCHF.sub.2                                                                             H    0 pyrrolidinothio-                                                                         CH                                                                   carbonyl                                                     6.106                                                                             OCHF.sub.2                                                                             H    0 piperidinothio-                                                                          CH                                                                   carbonyl                                                     6.107                                                                             OCHF.sub.2                                                                             H    0 N-phenylcarbamoyl-                                                                       CH                                                                   methyl                                                       6.108                                                                             OCHF.sub.2                                                                             H    0 2,4-dichlorophenyl                                                                       CH                                                 6.109                                                                             OCHF.sub.2                                                                             H    2 2,4-dichlorophenyl                                                                       CH                                                 6.110                                                                             OCHF.sub.2                                                                             H    0 CH.sub.2 COOH                                                                            CH                                                 6.111                                                                             OCHF.sub.2                                                                             H    0 CH.sub.2 COOCH.sub.3                                                                     CH                                                 6.112                                                                             OCHF.sub.2                                                                             H    0 CH.sub.2 CON(CH.sub.3).sub.2                                                             CH                                                 6.113                                                                             OCHF.sub.2                                                                             H    0 4-chlorophenyl                                                                           N                                                  6.114                                                                             OCHF.sub.2                                                                             H    0 p-tolyl   N                                                  6.115                                                                             OCHF.sub.2                                                                             furyl-2-                                                                            0 2-hydroxy-                                                                               CH                                                                   carbonylphenyl                                               6.116                                                                             OCHF.sub.2                                                                             furyl-2-                                                                            0 2-methoxy-                                                                               CH                                                                   carbonylphenyl                                               6.117                                                                             OCHF.sub.2                                                                             furyl-2-                                                                            0 phenyl    CH                                                 6.118                                                                             OCHF.sub.2                                                                             4-chloro-                                                                           0 2-hydroxy-                                                                               CH                                                            phenyl carbonylphenyl                                               6.119                                                                             OCHF.sub.2                                                                             4-chloro-                                                                           0 phenyl    CH                                                            phenyl                                                              6.120                                                                             OCHF.sub.2                                                                             CH.sub.3                                                                            0 4-chlorophenyl                                                                           CH                                                 6.121                                                                             Cl      H    2 p-tolyl   CH                                                 6.122                                                                             Cl      H    0 p-tolyl   CH                                                 6.123                                                                             Cl      H    2 4-chlorophenyl                                                                           CH                                                 6.124                                                                             Cl      H    0 4-chlorophenyl                                                                           CH                                                 6.125                                                                             Cl      H    0 acetyl    CH                                                 6.126                                                                             Cl      H    0 benzoyl   CH                                                 6.127                                                                             Cl      H    2 CH.sub.3  CH                                                 6.128                                                                             Cl      H    2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH                                                 6.129                                                                             Cl      H    2 CH(CH.sub.3).sub.2                                                                       CH                                                 6.130                                                                             Cl      H    2 benzyl    CH                                                 6.131                                                                             Cl      H    2 phenyl    CH                                                 6.132                                                                             Cl      H    0 phenyl    CH                                                 6.133                                                                             Cl      H    2 4-bromophenyl                                                                            CH                                                 6.134                                                                             Cl      H    0 4-bromophenyl                                                                            CH                                                 6.135                                                                             Cl      H    2 2-chlorophenyl                                                                           CH                                                 6.136                                                                             Cl      H    0 2-chlorophenyl                                                                           CH                                                 6.137                                                                             Cl      H    0 CH.sub.3 CH                                                  6.138                                                                             Cl      H    0 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                      CH                                                 6.139                                                                             Cl      H    0 CH(CH.sub.3).sub.2                                                                       CH                                                 6.140                                                                             Cl      H    0 benzyl    CH                                                 6.141                                                                             Cl      H    2 β-naphthyl                                                                          CH                                                 6.142                                                                             Cl      H    0 β-naphthyl                                                                          CH                                                 6.143                                                                             Cl      H    2 1,2,4-trichloro-                                                                         CH                                                                   phenyl                                                       6.144                                                                             Cl      H    0 1,2,4-trichloro-                                                                         CH                                                                   phenyl                                                       6.145                                                                             Cl      H    2 α-naphthyl                                                                         CH                                                 6.146                                                                             Cl      H    2 α-naphthyl                                                                         CH                                                 6.147                                                                             Cl      H    0 CH.sub.2 COOCH.sub.3                                                                     CH                                                 6.148                                                                             Cl      H    2 4-fluorophenyl                                                                           CH                                                 6.149                                                                             Cl      H    0 4-fluorophenyl                                                                           CH                                                 6.150                                                                             Cl      H    0 4-nitrophenyl                                                                            CH                                                 6.151                                                                             Cl      H    0 4-nitrophenyl                                                                            CH                                                 6.152                                                                             Cl      H    2 2-nitrophenyl                                                                            CH                                                 6.153                                                                             Cl      H    0 2-nitrophenyl                                                                            CH                                                 6.154                                                                             Cl      H    2 2-trifluoromethyl                                                                        CH                                                 6.155                                                                             Cl      H    0 2-trifluoromethyl                                                                        CH                                                 6.156                                                                             Cl      H    2 4-methoxyphenyl                                                                          CH                                                 6.157                                                                             Cl      H    0 4-methoxyphenyl                                                                          CH                                                 6.158                                                                             Cl      H    2 2-methoxyphenyl                                                                          CH                                                 6.159                                                                             Cl      H    0 2-methoxyphenyl                                                                          CH                                                 6.160                                                                             Cl      H    2 2,4,6-trimethyl-                                                                         CH                                                                   phenyl                                                       6.161                                                                             Cl      H    0 2,4,6-trimethyl-                                                                         CH                                                                   phenyl                                                       6.162                                                                             Cl      H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.163                                                                             Cl      H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                             CH                                                 6.164                                                                             Cl      H    0 CSN(CH.sub.2 CH.sub.3).sub.2                                                             CH                                                 6.165                                                                             Cl      H    0 pyrrolidinothio-                                                                         CH                                                                   carbonyl                                                     6.166                                                                             Cl      H    0 piperidinothio-                                                                          CH                                                                   carbonyl                                                     6.167                                                                             Cl      H    0 N-phenylcarbamoyl-                                                                       CH                                                                   methyl                                                       6.168                                                                             Cl      H    0 2,4-dichlorophenyl                                                                       CH                                                 6.169                                                                             Cl      H    2 2,4-dichlorophenyl                                                                       CH                                                 6.170                                                                             Cl      H    0 CH.sub.2 COOH                                                                            CH                                                 6.171                                                                             Cl      H    0 CH.sub.2 COOCH.sub.3                                                                     CH                                                 6.172                                                                             Cl      H    0 CH.sub.2 CON(CH.sub.3).sub. 2                                                            CH                                                 6.173                                                                             Cl      H    0 4-chlorophenyl                                                                           N                                                  6.174                                                                             Cl      H    0 p-tolyl   N                                                  6.175                                                                             Cl      furyl-2-                                                                            0 2-hydroxy-                                                                               CH                                                                   carbonylphenyl                                               6.176                                                                             Cl      furyl-2-                                                                            0 2-methoxy-                                                                               CH                                                                   carbonylphenyl                                               6.177                                                                             Cl      furyl-2-                                                                            0 phenyl    CH                                                 6.178                                                                             Cl      4-chloro-                                                                           0 2-hydroxy-                                                                               CH                                                            phenyl carbonylphenyl                                               6.179                                                                             Cl      4-chloro-                                                                           0 phenyl    CH                                                            phenyl                                                              6.180                                                                             Cl      CH.sub.3                                                                            0 4-chlorophenyl                                                                           CH                                                 6.181                                                                             OCH.sub.3                                                                              H    0 phenyl    CH                                                 6.182                                                                             OCH.sub.3                                                                              H    2 phenyl    CH                                                 6.183                                                                             OCH.sub.3                                                                              H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.184                                                                             OCH.sub.3                                                                              H    0 pyrrolidinothio-                                                                         CH                                                                   carbonyl                                                     6.185                                                                             OCH.sub.3                                                                              H    0 CH.sub.3  CH                                                 6.186                                                                             OCH.sub.3                                                                              H    2 CH.sub.3  CH                                                 6.187                                                                             NO.sub.2                                                                               H    0 phenyl    CH                                                 6.188                                                                             NO.sub.2                                                                               H    2 phenyl    CH                                                 6.189                                                                             NO.sub.2                                                                               H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.190                                                                             NO.sub.2                                                                               H    0 pyrrolidinothio-                                                                         CH                                                                   carbonyl                                                     6.191                                                                             NO.sub.2                                                                               H    0 CH.sub.3  CH                                                 6.192                                                                             NO.sub.2                                                                               H    2 CH.sub.3  CH                                                 6.193                                                                             CF.sub.3                                                                               H    0 phenyl    CH                                                 6.194                                                                             CF.sub.3                                                                               H    2 phenyl    CH                                                 6.195                                                                             CF.sub.3                                                                               H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.196                                                                             CF.sub.3                                                                               H    0 pyrrolidino-                                                                             CH                                                                   thiocarbonyl                                                 6.197                                                                             CF.sub.3                                                                               H    0 CH.sub.3  CH                                                 6.198                                                                             CF.sub.3                                                                               H    2 CH.sub.3  CH                                                 6.199                                                                             OSO.sub.2 CH.sub.3                                                                     H    0 phenyl    CH                                                 6.200                                                                             OSO.sub.2 CH.sub.3                                                                     H    2 phenyl    CH                                                 6.201                                                                             OSO.sub.2 CH.sub.3                                                                     H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.202                                                                             OSO.sub.2 CH.sub.3                                                                     H    0 pyrrolidino-                                                                             CH                                                                   thiocarbonyl                                                 6.203                                                                             OSO.sub.2 CH.sub.3                                                                     H    0 CH.sub.3  CH                                                 6.204                                                                             OSO.sub.2 CH.sub.3                                                                     H    2 CH.sub.3  CH                                                 6.205                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                            H    2 phenyl    CH                                                 6.206                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                            H    2 phenyl    CH                                                 6.207                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                            H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.208                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                            H    0 pyrrolidino-                                                                             CH                                                                   thiocarbonyl                                                 6.209                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                            H    2 CH.sub.3  CH                                                 6.210                                                                             OSO.sub.2 C.sub.3 H.sub.7 n                                                            H    0 CH.sub.3  CH                                                 6.211                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                             H    0 phenyl    CH                                                 6.212                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                             H    2 phenyl    CH                                                 6.213                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                             H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.214                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                             H    0 pyrrolidino-                                                                             CH                                                                   thiocarbonyl                                                 6.215                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                             H    0 CH.sub.3  CH                                                 6.216                                                                             SO.sub.2 N(CH.sub.3).sub.2                                                             H    2 CH.sub.3  CH                                                 6.217                                                                             CH.sub.3                                                                               H    0 phenyl    CH                                                 6.218                                                                             CH.sub.3                                                                               H    2 phenyl    CH                                                 6.219                                                                             CH.sub.3                                                                               H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.220                                                                             CH.sub.3                                                                               H    0 pyrrolidino-                                                                             CH                                                                   thiocarbonyl                                                 6.221                                                                             CH.sub.3                                                                               H    0 CH.sub.3  CH                                                 6.222                                                                             CH.sub.3                                                                               H    2 CH.sub.3  CH                                                 6.223                                                                             SO.sub.2 CH.sub.3                                                                      H    0 phenyl    CH                                                 6.224                                                                             SO.sub.2 CH.sub.3                                                                      H    2 phenyl    CH                                                 6.225                                                                             SO.sub.2 CH.sub.3                                                                      H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.226                                                                             SO.sub.2 CH.sub.3                                                                      H    0 pyrrolidino-                                                                             CH                                                                   thiocarbonyl                                                 6.227                                                                             SO.sub.2 CH.sub.3                                                                      H    0 CH.sub.3  CH                                                 6.228                                                                             SO.sub.2 CH.sub.3                                                                      H    2 CH.sub.3  CH                                                 6.229                                                                             phenyl  H    0 p-tolyl   CH 144-147°                                 6.230                                                                             phenyl  H    2 p-tolyl   CH 141-144° dec.                            6.231                                                                             COOCH.sub.3                                                                            H    2 benzyl    N                                                  6.232                                                                             COOCH.sub.3                                                                            H    2 phenyl    N                                                  6.233                                                                             OCF.sub.2 CHF.sub. 2                                                                   H    2 p-tolyl   CH 133-134°                                 6.234                                                                             OCF.sub.2 CHF.sub.2                                                                    H    2 p-tolyl   CH                                                 6.235                                                                             OCF.sub.2 CHF.sub.2                                                                    H    2 CH.sub.3  CH                                                 6.236                                                                             OCF.sub.2 CHF.sub.2                                                                    H    2 phenyl    CH                                                 6.237                                                                             OCF.sub.2 CHF.sub.2                                                                    H    2 4-chlorophenyl                                                                           CH                                                 6.238                                                                             OCF.sub.2 CHF.sub.2                                                                    H    2 β-naphthyl                                                                          CH                                                 6.239                                                                             F       H    0 4-chlorophenyl                                                                           CH                                                 6.240                                                                             F       H    0 β-naphthyl                                                                          CH 158-154°                                 6.241                                                                             F       H    2 β-naphthyl                                                                          CH                                                 6.242                                                                             COOCH.sub.3                                                                            H    2 2-methoxy-                                                                               CH  66-67°                                                    carbonylbenzyl                                               6.243                                                                             COOCH.sub.3                                                                            H    2 C.sub.3 H.sub.7 n                                                                        CH                                                 6.244                                                                             COOCH.sub.3                                                                            H    2 C.sub.2 H.sub.5                                                                          CH                                                 6.245                                                                             COOCH.sub.3                                                                            H    2 2-difluoromethoxy-                                                                       CH 145-147°                                                   phenyl                                                       6.246                                                                             COOCH.sub.3                                                                            H    2 3,4-dichlorophenyl                                                                       CH                                                 6.247                                                                             COOCH.sub.3                                                                            H    2 3,5-dichlorophenyl                                                                       CH                                                 6.248                                                                             COOCH.sub.3                                                                            H    2 3-chlorophenyl                                                                           CH                                                 6.249                                                                             COOCH.sub.3                                                                            H    2 2-difluoromethyl-                                                                        CH                                                                   thiophenyl                                                   6.250                                                                             COOCH.sub.3                                                                            H    2 3-trifluoromethyl-                                                                       CH                                                                   phenyl                                                       6.251                                                                             COOCH.sub.3                                                                            H    2 2,5-dimethyl-                                                                            CH                                                                   phenyl                                                       6.252                                                                             COOC.sub.2 H.sub.5                                                                     H    2 CH.sub.3  CH                                                 6.253                                                                             COOC.sub.2 H.sub.5                                                                     H    2 C.sub.3 H.sub.7 n                                                                        CH                                                 6.254                                                                             COOC.sub.2 H.sub.5                                                                     H    2 phenyl    CH 149°                                     6.255                                                                             COOC.sub.2 H.sub.5                                                                     H    2 p-tolyl   CH 147°                                     6.256                                                                             COOC.sub.2 H.sub.5                                                                     H    0 CSN(CH.sub.3).sub.2                                                                      CH                                                 6.257                                                                             NO.sub.2                                                                               H    2 p-tolyl   CH 149-151° (dec.)                          6.258                                                                             NO.sub.2                                                                               H    2 4-chlorophenyl                                                                           CH 164° (dec.)                              __________________________________________________________________________     No.                                                                               R.sup.1 (R.sup.2)                                                                      R.sup.5                                                                             m R.sup.9   E  m.p. (°C.)                               __________________________________________________________________________     6.259                                                                             NO.sub.2                                                                               H    2 4-bromophenyl                                                                            CH                                                 6.260                                                                             NO.sub.2                                                                               H    2 β-naphthyl                                                                          CH                                                 6.261                                                                             NO.sub.2                                                                               H    2 C.sub.2 H.sub.5                                                                          CH                                                 6.262                                                                             NO.sub.2                                                                               H    2 C.sub.3 H.sub.7 n                                                                        CH                                                 6.263                                                                             NO.sub.2                                                                               H    2 benzyl    CH                                                 6.264                                                                             NO.sub.2                                                                               H    2 2-methoxy-                                                                               CH                                                                   carbonylbenzyl                                               6.265                                                                             NO.sub.2                                                                               H    2 4-methoxy-                                                                               CH                                                                   phenyl                                                       6.266                                                                             NO.sub.2                                                                               H    2 2-difluoro-                                                                              CH                                                                   methoxyphenyl                                                6.267                                                                             NO.sub.2                                                                               H    2 mesityl   CH                                                 6.268                                                                             OCF.sub.3                                                                              H    2 p-tolyl   CH 138-139° (dec.)                          6.269                                                                             OC.sub.2 H.sub.4 OCH.sub.3                                                             H    2 p-tolyl   CH 135-137° (dec.)                          6.270                                                                             OC.sub.2 H.sub.4 Cl                                                                    H    2 p-tolyl   CH 133-135° (dec.)                          6.271                                                                             OCClCHCl     2 p-tolyl   CH 143-144° (dec.)                          6.272                                                                             CF.sub.3     2 p-tolyl   CH 156-158° (dec.)                          6.273                                                                             OSO.sub.2 CH.sub.3                                                                          2 p-tolyl   CH                                                 6.274                                                                             OSO.sub.2 N(CH.sub.3).sub.2                                                                 2 p-tolyl   CH                                                 6.275                                                                             OCH.sub.3    2 p-tolyl   CH 164° (dec.)                              6.276                                                                             OCH.sub.3    2 4-bromophenyl                                                                            CH 165° (dec.)                              6.277                                                                             OCH.sub.3    2 β-naphthyl                                                                          CH 148-150° (dec.)                          6.278                                                                             OCH.sub.3    2 benzyl    CH 126-128° (dec.)                          6.279                                                                             CF.sub.3     2 p-tolyl   CH 156-158° (dec.)                          6.280                                                                             CF.sub.3     2 4-chlorophenyl                                                                           CH 147-154° (dec.)                          6.281                                                                             CF.sub.3     2 β-naphthyl                                                                          CH 152-154° (dec.)                          __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________      ##STR44##                                                                     No  R.sup.1 R.sup.5                                                                            m  R.sup.9    E   m.p.(°C.)                             __________________________________________________________________________     7.001                                                                              COOCH.sub.3                                                                            H   2  p-tolyl    CH  153-158°                                                                dec.                                         7.002                                                                              COOCH.sub.3                                                                            H   0  p-tolyl    CH                                               7.003                                                                              COOCH.sub.3                                                                            H   2  4-chlorophenyl                                                                            CH                                               7.004                                                                              COOCH.sub.3                                                                            H   0  4-chlorophenyl                                                                            CH                                               7.005                                                                              COOCH.sub.3                                                                            H   0  acetyl     CH                                               7.006                                                                              COOCH.sub.3                                                                            H   0  benzoyl    CH                                               7.007                                                                              COOCH.sub.3                                                                            H   2  CH.sub.3   CH                                               7.008                                                                              COOCH.sub.3                                                                            H   2  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH                                               7.009                                                                              COOCH.sub.3                                                                            H   2  CH(CH.sub.3).sub.2                                                                        CH                                               7.010                                                                              COOCH.sub.3                                                                            H   2  benzyl     CH                                               7.011                                                                              COOCH.sub.3                                                                            H   2  phenyl     CH                                               7.012                                                                              COOCH.sub.3                                                                            H   0  phenyl     CH                                               7.013                                                                              COOCH.sub.3                                                                            H   2  4-bromophenyl                                                                             CH                                               7.014                                                                              COOCH.sub.3                                                                            H   0  4-bromophenyl                                                                             CH                                               7.015                                                                              COOCH.sub.3                                                                            H   2  2-chlorophenyl                                                                            CH                                               7.016                                                                              COOCH.sub.3                                                                            H   0  2-chlorophenyl                                                                            CH                                               7.017                                                                              COOCH.sub.3                                                                            H   0  CH.sub.3   CH                                               7.018                                                                              COOCH.sub.3                                                                            H   0  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH                                               7.019                                                                              COOCH.sub.3                                                                            H   0  CH(CH.sub.3).sub.2                                                                        CH                                               7.020                                                                              COOCH.sub.3                                                                            H   0  benzyl     CH                                               7.021                                                                              COOCH.sub.3                                                                            H   2  β-naphthyl                                                                           CH                                               7.022                                                                              COOCH.sub.3                                                                            H   0  β-naphthyl                                                                           CH                                               7.023                                                                              COOCH.sub.3                                                                            H   2  1,2,4-trichloro-                                                                          CH                                                                  phenyl                                                      7.024                                                                              COOCH.sub.3                                                                            H   0  1,2,4-trichloro-                                                                          CH                                                                  phenyl                                                      7.025                                                                              COOCH.sub.3                                                                            H   2  α-naphthyl                                                                          CH                                               7.026                                                                              COOCH.sub.3                                                                            H   2  α-naphthyl                                                                          CH                                               7.027                                                                              COOCH.sub.3                                                                            H   0  CH.sub.2 COOCH.sub.3                                                                      CH                                               7.028                                                                              COOCH.sub.3                                                                            H   2  4-fluorophenyl                                                                            CH                                               7.029                                                                              COOCH.sub.3                                                                            H   0  4-fluorophenyl                                                                            CH                                               7.030                                                                              COOCH.sub.3                                                                            H   0  4-nitrophenyl                                                                             CH                                               7.031                                                                              COOCH.sub.3                                                                            H   0  4-nitrophenyl                                                                             CH                                               7.032                                                                              COOCH.sub.3                                                                            H   2  2-nitorphenyl                                                                             CH                                               7.033                                                                              COOCH.sub.3                                                                            H   0  2-nitrophenyl                                                                             CH                                               7.034                                                                              COOCH.sub.3                                                                            H   2  2-trifluoromethyl                                                                         CH                                               7.035                                                                              COOCH.sub.3                                                                            H   0  2-trifluoromethyl                                                                         CH                                               7.036                                                                              COOCH.sub.3                                                                            H   2  4-methoxyphenyl                                                                           CH                                               7.037                                                                              COOCH.sub.3                                                                            H   0  4-methoxyphenyl                                                                           CH                                               7.038                                                                              COOCH.sub.3                                                                            H   2  2-methoxyphenyl                                                                           CH                                               7.039                                                                              COOCH.sub.3                                                                            H   0  2-methoxyphenyl                                                                           CH                                               7.040                                                                              COOCH.sub.3                                                                            H   2  2,4,6-trimethyl-                                                                          CH                                                                  phenyl                                                      7.041                                                                              COOCH.sub.3                                                                            H   0  2,4,6-trimethyl-                                                                          CH                                                                  phenyl                                                      7.042                                                                              COOCH.sub.3                                                                            H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.043                                                                              COOCH.sub.3                                                                            H   0  CSN(CH.sub.3 CH.sub.3).sub.2                                                              CH                                               7.044                                                                              COOCH.sub.3                                                                            H   0  CSN(CH.sub.2 CH.sub.3).sub.2                                                              CH                                               7.045                                                                              COOCH.sub.3                                                                            H   0  pyrrolidinothio-                                                                          CH                                                                  carbonyl                                                    7.046                                                                              COOCH.sub.3                                                                            H   0  piperidinothio-                                                                           CH                                                                  carbonyl                                                    7.047                                                                              COOCH.sub.3                                                                            H   0  N-phenylcarbamoyl-                                                                        CH                                                                  methyl                                                      7.048                                                                              COOCH.sub.3                                                                            H   0  2,4-dichlorophenyl                                                                        CH                                               7.049                                                                              COOCH.sub.3                                                                            H   2  2,4-dichlorophenyl                                                                        CH                                               7.050                                                                              COOCH.sub.3                                                                            H   0  CH.sub.2 COOH                                                                             CH                                               7.051                                                                              COOCH.sub.3                                                                            H   0  CH.sub.2 COOCH.sub.3                                                                      CH                                               7.052                                                                              COOCH.sub.3                                                                            H   0  CH.sub.2 CON(CH.sub.3).sub.2                                                              CH                                               7.053                                                                              COOCH.sub.3                                                                            H   0  4-chlorophenyl                                                                            N                                                7.054                                                                              COOCH.sub.3                                                                            H   0  p-tolyl    N                                                7.055                                                                              COOCH.sub.3                                                                            furyl-2-                                                                           0  2-hydroxy- CH                                                                  carbonylphenyl                                              7.056                                                                              COOCH.sub.3                                                                            furyl-2-                                                                           0  2-methoxy- CH                                                                  carbonylphenyl                                              7.057                                                                              COOCH.sub.3                                                                            furyl-2-                                                                           0  phenyl     CH                                               7.058                                                                              COOCH.sub.3                                                                            4-chloro-                                                                          0  2-hydroxy- CH                                                           phenyl carbonylphenyl                                              7.059                                                                              COOCH.sub.3                                                                            4-chloro-                                                                          0  phenyl     CH                                                           phenyl                                                             7.060                                                                              COOCH.sub.3                                                                            CH.sub.3                                                                           0  4-chlorophenyl                                                                            CH                                               7.061                                                                              OCHF.sub.2                                                                             H   2  p-tolyl    CH  146-150°                              7.062                                                                              OCHF.sub.2                                                                             H   0  p-tolyl    CH                                               7.063                                                                              OCHF.sub.2                                                                             H   2  4-chlorophenyl                                                                            CH                                               7.064                                                                              OCHF.sub.2                                                                             H   0  4-chlorophenyl                                                                            CH                                               7.065                                                                              OCHF.sub.2                                                                             H   0  acetyl     CH                                               7.066                                                                              OCHF.sub.2                                                                             H   0  benzoyl    CH                                               7.067                                                                              OCHF.sub.2                                                                             H   2  CH.sub.3   N                                                7.068                                                                              OCHF.sub.2                                                                             H   2  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH                                               7.069                                                                              OCHF.sub.2                                                                             H   2  CH(CH.sub.3).sub.2                                                                        CH                                               7.070                                                                              OCHF.sub.2                                                                             H   2  benzyl     CH                                               7.071                                                                              OCHF.sub.2                                                                             H   2  phenyl     CH                                               7.072                                                                              OCHF.sub.2                                                                             H   0  phenyl     CH                                               7.073                                                                              OCHF.sub.2                                                                             H   2  4-bromophenyl                                                                             CH                                               7.074                                                                              OCHF.sub.2                                                                             H   0  4-bromophenyl                                                                             CH                                               7.075                                                                              OCHF.sub.2                                                                             H   2  2-chlorophenyl                                                                            CH                                               7.076                                                                              OCHF.sub.2                                                                             H   0  2-chlorophenyl                                                                            CH                                               7.077                                                                              OCHF.sub.2                                                                             H   0  CH.sub.3   N                                                7.078                                                                              OCHF.sub.2                                                                             H   0  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH                                               7.079                                                                              OCHF.sub.2                                                                             H   0  CH(CH.sub.3).sub.2                                                                        CH                                               7.080                                                                              OCHF.sub.2                                                                             H   0  benzyl     CH                                               7.081                                                                              OCHF.sub.2                                                                             H   2  β-naphthyl                                                                           CH                                               7.082                                                                              OCHF.sub.2                                                                             H   0  β-naphthyl                                                                           CH  162-164°                              7.083                                                                              OCHF.sub.2                                                                             H   2  1,2,4-trichloro-                                                                          CH                                                                  phenyl                                                      7.084                                                                              OCHF.sub.2                                                                             H   0  2,4,5-trichloro-                                                                          CH  104-107°                                                 phenyl                                                      7.085                                                                              OCHF.sub.2                                                                             H   2  α-naphthyl                                                                          CH                                               7.086                                                                              OCHF.sub.2                                                                             H   2  α-naphthyl                                                                          CH                                               7.087                                                                              OCHF.sub.2                                                                             H   0  CH.sub.2 COOCH.sub.3                                                                      CH                                               7.088                                                                              OCHF.sub.2                                                                             H   2  4-fluorophenyl                                                                            CH                                               7.089                                                                              OCHF.sub.2                                                                             H   0  4-fluorophenyl                                                                            CH                                               7.090                                                                              OCHF.sub.2                                                                             H   0  4-nitrophenyl                                                                             CH                                               7.091                                                                              OCHF.sub.2                                                                             H   0  4-nitrophenyl                                                                             CH                                               7.092                                                                              OCHF.sub.2                                                                             H   2  2-nitrophenyl                                                                             CH                                               7.093                                                                              OCHF.sub.2                                                                             H   0  2-nitrophenyl                                                                             CH                                               7.094                                                                              OCHF.sub.2                                                                             H   2  2-trifluoromethyl                                                                         CH                                               7.095                                                                              OCHF.sub.2                                                                             H   0  2-trifluoromethyl                                                                         CH                                               7.096                                                                              OCHF.sub.2                                                                             H   2  4-methoxyphenyl                                                                           CH                                               7.097                                                                              OCHF.sub.2                                                                             H   0  4-methoxyphenyl                                                                           CH                                               7.098                                                                              OCHF.sub.2                                                                             H   2  2-methoxyphenyl                                                                           CH                                               7.099                                                                              OCHF.sub.2                                                                             H   0  2-methoxyphenyl                                                                           CH                                               7.100                                                                              OCHF.sub.2                                                                             H   2  2,4,6-trimethyl-                                                                          CH                                                                  phenyl                                                      7.101                                                                              OCHF.sub.2                                                                             H   0  2,4,6-trimethyl-                                                                          CH                                                                  phenyl                                                      7.102                                                                              OCHF.sub.2                                                                             H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.103                                                                              OCHF.sub.2                                                                             H   0  CSN(CH.sub.2 CH.sub.3).sub.2                                                              CH                                               7.104                                                                              OCHF.sub.2                                                                             H   0  CSN(CH.sub.2 CH.sub.3).sub.2                                                              CH                                               7.105                                                                              OCHF.sub.2                                                                             H   0  pyrrolidinothio-                                                                          CH                                                                  carbonyl                                                    7.106                                                                              OCHF.sub.2                                                                             H   0  piperidinothio-                                                                           CH                                                                  carbonyl                                                    7.107                                                                              OCHF.sub.2                                                                             H   0  N-phenylcarbamoyl-                                                                        CH                                                                  methyl                                                      7.108                                                                              OCHF.sub.2                                                                             H   0  2,4-dichlorophenyl                                                                        CH                                               7.109                                                                              OCHF.sub.2                                                                             H   2  2,4-dichlorophenyl                                                                        CH                                               7.110                                                                              OCHF.sub.2                                                                             H   0  CH.sub.2 COOH                                                                             CH                                               7.111                                                                              OCHF.sub.2                                                                             H   0  CH.sub.2 COOCH.sub.3                                                                      CH                                               7.112                                                                              OCHF.sub.2                                                                             H   0  CH.sub.2 CON(CH.sub.3).sub.2                                                              CH                                               7.113                                                                              OCHF.sub.2                                                                             H   0  4-Chlorophenyl                                                                            N                                                7.114                                                                              OCHF.sub.2                                                                             H   0  p-tolyl    N                                                7.115                                                                              OCHF.sub.2                                                                             furyl-2-                                                                           0  2-hydroxy- CH                                                                  carbonylphenyl                                              7.116                                                                              OCHF.sub.2                                                                             furyl-2-                                                                           0  2-methoxy- CH                                                                  carbonylphenyl                                              7.117                                                                              OCHF.sub.2                                                                             furyl-2-                                                                           0  phenyl     CH                                               7.118                                                                              OCHF.sub.2                                                                             4-chloro-                                                                          0  2-hydroxy- CH                                                           phenyl carbonylphenyl                                              7.119                                                                              OCHF.sub.2                                                                             4-chloro-                                                                          0  phenyl     CH                                                           phenyl                                                             7.120                                                                              OCHF.sub.2                                                                             CH.sub.3                                                                           0  4-chlorophenyl                                                                            CH                                               7.121                                                                              Cl      H   2  p-tolyl    CH                                               7.122                                                                              Cl      H   0  p-tolyl    CH                                               7.123                                                                              Cl      H   2  4-chlorophenyl                                                                            CH                                               7.124                                                                              Cl      H   0  4-chlorophenyl                                                                            CH                                               7.125                                                                              Cl      H   0  acetyl     CH                                               7.126                                                                              Cl      H   0  benzoyl    CH                                               7.127                                                                              Cl      H   2  CH.sub.3   CH                                               7.128                                                                              Cl      H   2  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH                                               7.129                                                                              Cl      H   2  CH(CH.sub.3).sub.2                                                                        CH                                               7.130                                                                              Cl      H   2  benzyl     CH                                               7.131                                                                              Cl      H   2  phenyl     CH                                               7.132                                                                              Cl      H   0  phenyl     CH                                               7.133                                                                              Cl      H   2  4-bromophenyl                                                                             CH                                               7.134                                                                              Cl      H   0  4-bromophenyl                                                                             CH                                               7.135                                                                              Cl      H   2  2-chlorophenyl                                                                            CH                                               7.136                                                                              Cl      H   0  2-chloropehnyl                                                                            CH                                               7.137                                                                              Cl      H   0  CH.sub.3 CH                                                 7.138                                                                              Cl      H   0  CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       CH                                               7.139                                                                              Cl      H   0  CH(CH.sub.3).sub.2                                                                        CH                                               7.140                                                                              Cl      H   0  benzyl     CH                                               7.141                                                                              Cl      H   2  β-naphthyl                                                                           CH                                               7.142                                                                              Cl      H   0  β-naphthyl                                                                           CH  156-158°                                                                dec.                                         7.143                                                                              Cl      H   2  1,2,4-trichloro-                                                                          CH                                                                  phenyl                                                      7.144                                                                              Cl      H   0  1,2,4-trichloro-                                                                          CH                                                                  phenyl                                                      7.145                                                                              Cl      H   2  α-naphthyl                                                                          CH                                               7.146                                                                              Cl      H   2  α-naphthyl                                                                          CH                                               7.147                                                                              Cl      H   0  CH.sub.2 COOCH.sub.3                                                                      CH                                               7.148                                                                              Cl      H   2  4-fluorophenyl                                                                            CH                                               7.149                                                                              Cl      H   0  4-fluorophenyl                                                                            CH                                               7.150                                                                              Cl      H   0  4-nitrophenyl                                                                             CH                                               7.151                                                                              Cl      H   0  4-nitrophenyl                                                                             CH                                               7.152                                                                              Cl      H   2  2-nitrophenyl                                                                             CH                                               7.153                                                                              Cl      H   0  2-nitrophenyl                                                                             CH                                               7.154                                                                              Cl      H   2  2-trifluoromethyl                                                                         CH                                               7.155                                                                              Cl      H   0  2-trifluoromethyl                                                                         CH                                               7.156                                                                              Cl      H   2  4-methoxyphenyl                                                                           CH                                               7.157                                                                              Cl      H   0  4-methoxyphenyl                                                                           CH                                               7.158                                                                              Cl      H   2  2-methoxyphenyl                                                                           CH                                               7.159                                                                              Cl      H   0  2-methoxyphenyl                                                                           CH                                               7.160                                                                              Cl      H   2  2,4,6-trimethyl-                                                                          CH                                                                  phenyl                                                      7.161                                                                              Cl      H   0  2,4,6-trimethyl-                                                                          CH                                                                  phenyl                                                      7.162                                                                              Cl      H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.163                                                                              Cl      H   0  CSN(CH.sub.2 CH.sub.3).sub.2                                                              CH                                               7.164                                                                              Cl      H   0  CSN(CH.sub.2 CH.sub.3).sub.2                                                              CH                                               7.165                                                                              Cl      H   0  pyrrolidinothio-                                                                          CH                                                                  carbonyl                                                    7.166                                                                              Cl      H   0  piperidinothio-                                                                           CH                                                                  carbonyl                                                    7.167                                                                              Cl      H   0  N-phenylcarbamoyl-                                                                        CH                                                                  methyl                                                      7.168                                                                              Cl      H   0  2,4-dichlorophenyl                                                                        CH                                               7.169                                                                              Cl      H   2  2,4-dichlorophenyl                                                                        CH                                               7.170                                                                              Cl      H   0  CH.sub.2 COOH                                                                             CH                                               7.171                                                                              Cl      H   0  CH.sub.2 COOCH.sub.3                                                                      CH                                               7.172                                                                              Cl      H   0  CH.sub.2 CON(CH.sub.3).sub.2                                                              CH                                               7.173                                                                              Cl      H   0  4-chlorophenyl                                                                            N                                                7.174                                                                              Cl      H   0  p-tolyl    N                                                7.175                                                                              Cl      furyl-2-                                                                           0  2-hydroxy- CH                                                                  carbonylphenyl                                              7.176                                                                              Cl      furyl-2-                                                                           0  2-methoxy- CH                                                                  carbonylphenyl                                              7.177                                                                              Cl      furyl-2-                                                                           0  phenyl     CH                                               7.178                                                                              Cl      4-chloro-                                                                          0  2-hydroxy- CH                                                           phenyl carbonylphenyl                                              7.179                                                                              Cl      4-chloro-                                                                          0  phenyl     CH                                                           phenyl                                                             7.180                                                                              Cl      CH.sub.3                                                                           0  4-chlorophenyl                                                                            CH                                               7.181                                                                              OCH.sub.3                                                                              H   0  phenyl     CH                                               7.182                                                                              OCH.sub.3                                                                              H   2  phenyl     CH                                               7.183                                                                              OCH.sub.3                                                                              H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.184                                                                              OCH.sub.3                                                                              H   0  pyrrolidinothio-                                                                          CH                                                                  carbonyl                                                    7.185                                                                              OCH.sub.3                                                                              H   0  CH.sub.3   CH                                               7.186                                                                              OCH.sub.3                                                                              H   2  CH.sub.3   CH                                               7.187                                                                              NO.sub.2                                                                               H   0  phenyl     CH                                               7.188                                                                              NO.sub.2                                                                               H   2  phenyl     CH                                               7.189                                                                              NO.sub.2                                                                               H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.190                                                                              NO.sub.2                                                                               H   0  pyrrolidinothio-                                                                          CH                                                                  carbonyl                                                    7.191                                                                              NO.sub.2                                                                               H   0  CH.sub.3   CH                                               7.192                                                                              NO.sub.2                                                                               H   2  CH.sub.3   CH                                               7.193                                                                              CF.sub.3                                                                               H   0  phenyl     CH                                               7.194                                                                              CF.sub.3                                                                               H   2  phenyl     CH                                               7.195                                                                              CF.sub.3                                                                               H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.196                                                                              CF.sub.3                                                                               H   0  pyrrolidino-                                                                              CH                                                                  thiocarbonyl                                                7.197                                                                              CF.sub.3                                                                               H   0  CH.sub.3   CH                                               7.198                                                                              CF.sub.3                                                                               H   2  CH.sub.3   CH                                               7.199                                                                              OSO.sub.2 CH.sub.3                                                                     H   0  phenyl     CH                                               7.200                                                                              OSO.sub.2 CH.sub.3                                                                     H   2  phenyl     CH                                               7.201                                                                              OSO.sub.2 CH.sub.3                                                                     H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.202                                                                              OSO.sub.2 CH.sub.3                                                                     H   0  pyrrolidino-                                                                              CH                                                                  thiocarbonyl                                                7.203                                                                              OSO.sub.2 CH.sub.3                                                                     H   0  CH.sub.3   CH                                               7.204                                                                              OSO.sub.2 CH.sub.3                                                                     H   2  CH.sub.3   CH                                               7.205                                                                              OSO.sub.2 C.sub.3 H.sub.7 n                                                            H   2  phenyl     CH                                               7.206                                                                              OSO.sub.2 C.sub.3 H.sub.7 n                                                            H   2  phenyl     CH                                               7.207                                                                              OSO.sub.2 C.sub.3 H.sub.7 n                                                            H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.208                                                                              OSO.sub.2 C.sub.3 H.sub.7 n                                                            H   0  pyrrolidino-                                                                              CH                                                                  thiocarbonyl                                                7.209                                                                              OSO.sub.2 C.sub.3 H.sub.7 n                                                            H   2  CH.sub.3   CH                                               7.210                                                                              OSO.sub.2 C.sub.3 H.sub.7 n                                                            H   0  CH.sub.3   CH                                               7.211                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H   0  phenyl     CH                                               7.212                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H   2  phenyl     CH                                               7.213                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H   0  CSN(CH.sub. 3).sub.2                                                                      CH                                               7.214                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H   0  pyrrolidino-                                                                              CH                                                                  thiocarbonyl                                                7.215                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H   0  CH.sub.3   CH                                               7.216                                                                              SO.sub.2 N(CH.sub.3).sub.2                                                             H   2  CH.sub.3   CH                                               7.217                                                                              CH.sub.3                                                                               H   0  phenyl     CH                                               7.218                                                                              CH.sub.3                                                                               H   2  phenyl     CH                                               7.219                                                                              CH.sub.3                                                                               H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.220                                                                              CH.sub.3                                                                               H   0  pyrrolidino-                                                                              CH                                                                  thiocarbonyl                                                7.221                                                                              CH.sub.3                                                                               H   0  CH.sub.3   CH                                               7.222                                                                              CH.sub.3                                                                               H   2  CH.sub.3   CH                                               7.223                                                                              SO.sub.2 CH.sub.3                                                                      H   0  phenyl     CH                                               7.224                                                                              SO.sub.2 CH.sub.3                                                                      H   2  phenyl     CH                                               7.225                                                                              SO.sub.2 CH.sub.3                                                                      H   0  CSN(CH.sub.3).sub.2                                                                       CH                                               7.226                                                                              SO.sub.2 CH.sub.3                                                                      H   0  pyrrolidino-                                                                              CH                                                                  thiocarbonyl                                                7.227                                                                              SO.sub.2 CH.sub.3                                                                      H   0  CH.sub.3   CH                                               7.228                                                                              SO.sub.2 CH.sub.3                                                                      H   2  CH.sub.3   CH                                               7.229                                                                              CF.sub.3                                                                               H   2  β-naphthyl                                                                           CH  153-156°                                                                dec.                                         7.230                                                                              2,6-Cl.sub.2                                                                           H   2  β-naphthyl                                                                           CH  154-158°                                                                dec.                                         7.231                                                                              phenyl  H   2  CH.sub.3   CH  166-170°                                                                dec.                                         7.232                                                                              phenyl  H   2  p-tolyl    CH  156-159°                                                                dec.                                         7.233                                                                              phenyl  H   0  4-chlorophenyl                                                                            CH  161-154°                              7.234                                                                              F       H   0  4-chlorophenyl                                                                            CH  126-127°                              7.235                                                                              phenyl  H   0  CH.sub.2 COOCH.sub.3                                                                      CH  127-129°                              7.236                                                                              NO.sub.2                                                                               H   0  anilidocarbonyl-                                                                          CH  162-165°                                                 methyl         (dec.)                                       7.237                                                                              2-Cl,6-CH.sub.3                                                                        H   2  p-tolyl    CH  150-152°                                                                (dec.)                                       __________________________________________________________________________

                  TABLE 8                                                          ______________________________________                                          ##STR45##                                                                     NO   R.sup.1   m     R.sup.9   R.sup.3 m.p. (°C.)                       ______________________________________                                         8.001                                                                               COOCH.sub.3                                                                              0     p-tolyl   CH.sub.3                                        8.002                                                                               COOCH.sub.3                                                                              0     p-tolyl   OCH.sub.3                                       8.003                                                                               COOCH.sub.3                                                                              0     p-tolyl   OCHF.sub.2                                      8.004                                                                               COOCH.sub.3                                                                              2     p-tolyl   CH.sub.3                                        8.005                                                                               COOCH.sub.3                                                                              2     p-tolyl   OCH.sub.3                                       8.006                                                                               COOCH.sub.3                                                                              2     p-tolyl   OCHF.sub.2                                      8.007                                                                               COOCH.sub.3                                                                              0     CSN(CH.sub.3).sub.2                                                                      CH.sub.3                                        8.008                                                                               COOCH.sub.3                                                                              0     CSN(CH.sub.3).sub.2                                                                      OCH.sub.3                                       8.009                                                                               COOCH.sub.3                                                                              0     CSN(CH.sub.3).sub.2                                                                      OCHF.sub.2                                      8.010                                                                               COOCH.sub.3                                                                              2     ethyl     CH.sub.3                                        8.011                                                                               COOCH.sub.3                                                                              2     ethyl     OCH.sub.3                                       8.012                                                                               COOCH.sub.3                                                                              2     ethyl     OCHF.sub.2                                      8.013                                                                               COOCH.sub.3                                                                              0     4-chlorophenyl                                                                           CH.sub.3                                        8.014                                                                               COOCH     0     4-chlorophenyl                                                                           OCHF.sub.2                                      8.015                                                                               COOCH.sub.3                                                                              0     4-chlorophenyl                                                                           OCH.sub.3                                       8.016                                                                               COOCH.sub.3                                                                              2     4-chlorophenyl                                                                           CH.sub.3                                        8.017                                                                               COOCH.sub.3                                                                              2     4-chlorophenyl                                                                           OCHF.sub.2                                      8.018                                                                               COOCH.sub.3                                                                              2     4-chlorophenyl                                                                           OCH.sub.3                                       8.019                                                                               COOCH.sub.3                                                                              0     pyrrolidino                                                                    thiocarbonyl                                                                             CH.sub.3                                        8.020                                                                               COOCH.sub.3                                                                              0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCH.sub.2                                       8.021                                                                               COOCH.sub.3                                                                              0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCHF.sub.2                                      8.022                                                                               OCHF.sub.2                                                                               0     p-tolyl   CH.sub.3                                        8.023                                                                               OCHF.sub.2                                                                               0     p-tolyl   OCH.sub.3                                       8.024                                                                               OCHF.sub.2                                                                               0     p-tolyl   OCHF.sub.2                                      8.025                                                                               OCHF.sub.2                                                                               2     p-tolyl   CH.sub.3                                                                               154-158°                                                                dec.                                    8.026                                                                               OCHF.sub.2                                                                               2     p-tolyl   OCH.sub.3                                       8.027                                                                               OCHF.sub.2                                                                               2     p-tolyl   OCHF.sub.2                                      8.028                                                                               OCHF.sub.2                                                                               0     CSN(CH.sub.3).sub.2                                                                      CH.sub.3                                        8.029                                                                               OCHF.sub.2                                                                               0     CSN(CH.sub.3).sub.2                                                                      OCH.sub.3                                       8.030                                                                               OCHF.sub.2                                                                               0     CSN(CH.sub.3).sub.2                                                                      OCHF.sub.2                                      8.031                                                                               OCHF.sub.2                                                                               2     ethyl     CH.sub.3                                        8.032                                                                               OCHF.sub.2                                                                               2     ethyl     OCH.sub.3                                       8.033                                                                               OCHF.sub.2                                                                               2     ethyl     OCHF.sub.2                                      8.034                                                                               OCHF.sub.2                                                                               0     4-chlorophenyl                                                                           CH.sub.3                                        8.035                                                                               OCHF.sub.2                                                                               0     4-chlorophenyl                                                                           OCHF.sub.2                                      8.036                                                                               OCHF.sub.2                                                                               0     4-chlorophenyl                                                                           OCH.sub.3                                       8.037                                                                               OCHF.sub.2                                                                               2     4-chlorophenyl                                                                           CH.sub.3                                        8.038                                                                               OCHF.sub.2                                                                               2     4-chlorophenyl                                                                           OCHF.sub.2                                      8.039                                                                               OCHF.sub.2                                                                               2     4-chlorophenyl                                                                           OCH.sub.3                                       8.040                                                                               OCHF.sub.2                                                                               0     pyrrolidino                                                                    thiocarbonyl                                                                             CH.sub.3                                        8.041                                                                               OCHF.sub.2                                                                               0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCH.sub.2                                       8.042                                                                               OCHF.sub.2                                                                               0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCHF.sub.2                                      8.043                                                                               Cl        0     p-tolyl   CH.sub.3                                        8.044                                                                               Cl        0     p-tolyl   OCH.sub.3                                       8.045                                                                               Cl        0     p-tolyl   OCHF.sub.2                                      8.046                                                                               Cl        2     p-tolyl   CH.sub.3                                        8.047                                                                               Cl        2     p-tolyl   OCH.sub.3                                       8.048                                                                               Cl        2     p-tolyl   OCHF.sub.2                                      8.049                                                                               Cl        0     CSN(CH.sub.3).sub.2                                                                      CH.sub.3                                        8.050                                                                               Cl        0     CSN(CH.sub.3).sub.2                                                                      OCH.sub.3                                       8.051                                                                               Cl        0     CSN(CH.sub.3).sub.2                                                                      OCHF.sub.2                                      8.052                                                                               Cl        2     ethyl     CH.sub.3                                        8.053                                                                               Cl        2     ethyl     OCH.sub.3                                       8.054                                                                               Cl        2     ethyl     OCHF.sub.2                                      8.055                                                                               Cl        0     4-chlorophenyl                                                                           CH.sub.3                                        8.056                                                                               Cl        0     4-chlorophenyl                                                                           OCHF.sub.2                                      8.057                                                                               Cl        0     4-chlorophenyl                                                                           OCH.sub.3                                       8.058                                                                               Cl        2     4-chlorophenyl                                                                           CH.sub.3                                        8.059                                                                               Cl        2     4-chlorophenyl                                                                           OCHF.sub.2                                      8.060                                                                               Cl        2     4-chlorophenyl                                                                           OCH.sub.3                                       8.061                                                                               Cl        0     pyrrolidino-                                                                   thiocarbonyl                                                                             CH.sub.3                                        8.062                                                                               Cl        0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCH.sub.2                                       8.063                                                                               Cl        0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCHF.sub.2                                      8.064                                                                               NO.sub.2  0     p-tolyl   CH.sub.3                                        8.065                                                                               NO.sub.2  0     p-tolyl   OCH.sub.3                                       8.066                                                                               NO.sub.2  0     p-tolyl   OCHF.sub.2                                      8.067                                                                               NO.sub.2  2     p-tolyl   CH.sub.3                                        8.068                                                                               NO.sub.2  2     p-tolyl   OCH.sub.3                                       8.069                                                                               NO.sub.2  2     p-tolyl   OCHF.sub.2                                      8.070                                                                               NO.sub.2  0     CSN(CH.sub.3).sub.2                                                                      CH.sub.3                                        8.071                                                                               NO.sub.2  0     CSN(CH.sub.3).sub.2                                                                      OCH.sub.3                                       8.072                                                                               NO.sub.2  0     CSN(CH.sub.3).sub.2                                                                      OCHF.sub.2                                      8.073                                                                               NO.sub.2  2     ethyl     CH.sub.3                                        8.074                                                                               NO.sub.2  2     ethyl     OCH.sub.3                                       8.075                                                                               NO.sub.2  2     ethyl     OCHF.sub.2                                      8.076                                                                               NO.sub.2  0     4-chlorophenyl                                                                           CH.sub.3                                        8.077                                                                               NO.sub.2  0     4-chlorophenyl                                                                           OCHF.sub.2                                      8.078                                                                               NO.sub.2  0     4-chlorophenyl                                                                           OCH.sub.3                                       8.079                                                                               NO.sub.2  2     4-chlorophenyl                                                                           CH.sub.3                                        8.080                                                                               NO.sub.2  2     4-chlorophenyl                                                                           OCHF.sub.2                                      8.081                                                                               NO.sub.2  2     4-chlorophenyl                                                                           OCH.sub.3                                       8.082                                                                               NO.sub.2  0     pyrrolidino-                                                                   thiocarbonyl                                                                             CH.sub.3                                        8.083                                                                               NO.sub.2  0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCH.sub.2                                       8.084                                                                               NO.sub.2  0     pyrrolidino-                                                                   thiocarbonyl                                                                             OCHF.sub.2                                      8.085                                                                               COOCH.sub.3                                                                              0     CH.sub.3  CH.sub.3                                        8.086                                                                               COOCH.sub.3                                                                              0     CH.sub.3  OCH.sub.3                                       8.087                                                                               COOCH.sub.3                                                                              0     CH.sub.3  OCHF.sub.2                                      8.088                                                                               COOCH.sub.3                                                                              2     CH.sub.3  CH.sub.3                                        8.089                                                                               COOCH.sub.3                                                                              2     CH.sub.3  OCH.sub.3                                       8.090                                                                               COOCH.sub.3                                                                              2     CH.sub.3  OCHF.sub.2                                      8.091                                                                               OCHF.sub.2                                                                               0     CH.sub.3  CH.sub.3                                        8.092                                                                               OCHF.sub.2                                                                               0     CH.sub.3  OCHF.sub.2                                      8.093                                                                               OCHF.sub.2                                                                               0     CH.sub.3  OCH.sub.3                                       8.094                                                                               OCHF.sub.2                                                                               2     CH.sub.3  CH.sub.3                                        8.095                                                                               OCHF.sub.2                                                                               2     CH.sub.3  OCH.sub.3                                       8.096                                                                               OCHF.sub.2                                                                               2     CH.sub.3  OCHF.sub.2                                      8.097                                                                               NO.sub.2  2     CH.sub.2 COOH                                                                            CH.sub.3                                                                               139-141°                                                                (dec.)                                  8.098                                                                               OCH.sub.3 2     CH.sub.3  CH.sub.3                                                                               148° (dec.)                      8.099                                                                               CF.sub.3  2     CH.sub.3  CH.sub.3                                                                               159-160°                                                                (dec.)                                  ______________________________________                                    

                                      TABLE 9                                      __________________________________________________________________________      ##STR46##                                                                     No R.sup.1                                                                              m R.sup.9 R.sup.3                                                                               R.sup.4                                                                            E  m.p. (°C.)                             __________________________________________________________________________     9.001                                                                             COOCH.sub.3                                                                          0 pyrrolidino-                                                                           CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.002                                                                             COOCH.sub.3                                                                          0 pyrrolidino-                                                                           OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                                          thiocarbonyl                                                        9.003                                                                             COOCH.sub.3                                                                          0 pyrrolidino-                                                                           Cl     OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.004                                                                             COOCH.sub.3                                                                          0 pyrrolidino-                                                                           N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.005                                                                             COOCH.sub.3                                                                          0 pyrrolidino-                                                                           CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.006                                                                             COOCH.sub.3                                                                          0 pyrrolidino-                                                                           CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.007                                                                             COOCH.sub.3                                                                          0 dimethylthio-                                                                          CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.008                                                                             COOCH.sub.3                                                                          0 dimethylthio-                                                                          OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                                          carbamoyl                                                           9.009                                                                             COOCH.sub.3                                                                          0 dimethylthio-                                                                          Cl     OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.010                                                                             COOCHhd 3                                                                            0 dimethylthio-                                                                          N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.011                                                                             COOCH.sub.3                                                                          0 dimethylthio-                                                                          CH(OCH.sub.3)                                                                         OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.012                                                                             COOCH.sub.3                                                                          0 benzoyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.013                                                                             COOCH.sub.3                                                                          0 benzoyl OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.014                                                                             COOCH.sub.3                                                                          0 benzoyl Cl     OCH.sub.3                                                                          N                                                9.015                                                                             COOCH.sub.3                                                                          0 benzoyl N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.016                                                                             COOCH.sub.3                                                                          0 benzoyl CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.017                                                                             COOCH.sub.3                                                                          0 benzoyl CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.018                                                                             COOCH.sub.3                                                                          0 acetyl  CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.019                                                                             COOCH.sub.3                                                                          0 acetyl  OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.020                                                                             COOCH.sub.3                                                                          0 acetyl  Cl     OCH.sub.3                                                                          N                                                9.021                                                                             COOCH.sub.3                                                                          0 acetyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.022                                                                             COOCH.sub.3                                                                          0 acetyl  CH(OCH.sub.3).sub.2                                                                   OCH.sub. 3                                                                         CH                                               9.023                                                                             COOCH.sub.3                                                                          0 acetyl  CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.024                                                                             OCHF.sub.2                                                                           0 pyrrolidino-                                                                           CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.025                                                                             OCHF.sub.2                                                                           0 pyrrolidino-                                                                           OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                                          thiocarbonyl                                                        9.026                                                                             OCHF.sub.2                                                                           0 pyrrolidino-                                                                           Cl     OCH.sub.3                                                                          CH 143-144°                                          thiocarbonyl          dec.                                          9.027                                                                             OCHF.sub.2                                                                           0 pyrrolidino-                                                                           N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.028                                                                             OCHF.sub.2                                                                           0 pyrrolidino-                                                                           CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.029                                                                             OCHF.sub.2                                                                           0 pyrrolidino-                                                                           CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.030                                                                             OCHF.sub.2                                                                           0 dimethylthio-                                                                          CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.031                                                                             OCHF.sub.2                                                                           0 dimethylthio-                                                                          OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                                          carbamoyl                                                           9.032                                                                             OCHF.sub.2                                                                           0 dimethylthio-                                                                          Cl     OCH.sub.3                                                                          N                                                           carbamoyl                                                           9.033                                                                             OCHF.sub.2                                                                           0 dimethylthio-                                                                          N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                           carbamoyl                                                           9.034                                                                             OCHF.sub.2                                                                           0 dimethylthio-                                                                          CH(OCH.sub.3)                                                                         OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.035                                                                             OCHF.sub.2                                                                           0 benzoyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.036                                                                             OCHF.sub. 2                                                                          0 benzoyl OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.037                                                                             OCHF.sub.2                                                                           0 benzoyl Cl     OCH.sub.3                                                                          N                                                9.038                                                                             OCHF.sub.2                                                                           0 benzoyl N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                               9.039                                                                             OCHF.sub.2                                                                           0 benzoyl CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.040                                                                             OCHF.sub.2                                                                           0 benzoyl CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.041                                                                             OCHF.sub.2                                                                           0 acetyl  CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.042                                                                             OCHF.sub.2                                                                           0 acetyl  OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.043                                                                             OCHF.sub.2                                                                           0 acetyl  Cl     OCH.sub.3                                                                          CH                                               9.044                                                                             OCHF.sub.2                                                                           0 acetyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.045                                                                             OCHF.sub.2                                                                           0 acetyl  CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.046                                                                             OCHF.sub.2                                                                           0 acetyl  CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.047                                                                             Cl    0 pyrrolidino-                                                                           CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.048                                                                             Cl    0 pyrrolidino-                                                                           OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                                          thiocarbonyl                                                        9.049                                                                             Cl    0 pyrrolidino-                                                                           Cl     OCH.sub.3                                                                          CH 141-143°                                          thiocarbonyl          dec.                                          9.050                                                                             Cl    0 pyrrolidino                                                                            N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                           thiocarbonyl                                                        9.051                                                                             Cl    0 pyrrolidino-                                                                           CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.052                                                                             Cl    0 pyrrolidino-                                                                           CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                                          thiocarbonyl                                                        9.053                                                                             Cl    0 dimethylthio-                                                                          CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.054                                                                             Cl    0 dimethylthio-                                                                          OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                                          carbamoyl                                                           9.055                                                                             Cl    0 dimethylthio-                                                                          Cl     OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.056                                                                             Cl    0 dimethylthio-                                                                          N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.057                                                                             Cl    0 dimethylthio-                                                                          CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                                          carbamoyl                                                           9.058                                                                             Cl    0 benzoyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.059                                                                             Cl    0 benzoyl OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.060                                                                             Cl    0 benzoyl Cl     OCH.sub.3                                                                          N                                                9.061                                                                             Cl    0 benzoyl N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                               9.062                                                                             Cl    0 benzoyl CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.063                                                                             Cl    0 benzoyl CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.064                                                                             Cl    0 acetyl  CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.065                                                                             Cl    0 acetyl  OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.066                                                                             Cl    0 acetyl  Cl     OCH.sub.3                                                                          CH                                               9.067                                                                             Cl    0 acetyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.068                                                                             Cl    0 acetyl  CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.069                                                                             Cl    0 acetyl  CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.070                                                                             COOCH.sub.3                                                                          0 2-chlorophenyl                                                                         CH.sub.2 CH.sub.3                                                                     OCH.sub.3                                                                          CH                                               9.071                                                                             COOCH.sub.3                                                                          2 2-chlorophenyl                                                                         CH.sub.2 CH.sub.3                                                                     OCH.sub.3                                                                          CH                                               9.072                                                                             COOCH.sub.3                                                                          0 2-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          N                                                9.073                                                                             COOCH.sub.3                                                                          2 2-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          CH                                               9.074                                                                             COOCH.sub.3                                                                          0 2-chlorophenyl                                                                         N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.075                                                                             COOCH.sub.3                                                                          2 2-chlorophenyl                                                                         N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                               9.076                                                                             COOCH.sub.3                                                                          0 CH.sub.2 CH.sub.3                                                                      Cl     OCH.sub.3                                                                          N                                                9.077                                                                             COOCH.sub.3                                                                          2 CH.sub.2 CH.sub.3                                                                      Cl     OCH.sub.3                                                                          CH                                               9.078                                                                             COOCH.sub.3                                                                          0 CH.sub.2 CH.sub.3                                                                      CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.079                                                                             COOCH.sub.3                                                                          2 CH.sub.2 CH.sub.3                                                                      CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.080                                                                             COOCH.sub.3                                                                          0 p-tolyl OCH.sub.3                                                                             Cl  CH                                               9.081                                                                             COOCH.sub.3                                                                          2 p-tolyl OCH.sub.3                                                                             Cl  N                                                9.082                                                                             COOCH.sub.3                                                                          0 p-tolyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.083                                                                             COOCH.sub.3                                                                          2 p-tolyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.084                                                                             OCHF.sub.2                                                                           0 p-tolyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.085                                                                             OCHF.sub.2                                                                           2 p-tolyl CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH 154-157°                                                                dec.                                          9.086                                                                             COOCH.sub.3                                                                          0 methyl  CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.087                                                                             COOCH.sub.3                                                                          0 methyl  OCH.sub.2 CH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.088                                                                             COOCH.sub.3                                                                          0 methyl  Cl     OCH.sub.3                                                                          CH                                               9.089                                                                             COOCH.sub.3                                                                          0 methyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                               9.090                                                                             COOCH.sub.3                                                                          0 methyl  CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.091                                                                             COOCH.sub.3                                                                          0 methyl  CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.092                                                                             COOCH.sub.3                                                                          2 methyl  CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.093                                                                             COOCH.sub.3                                                                          2 methyl  OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.094                                                                             COOCH.sub.3                                                                          2 methyl  Cl     OCH.sub.3                                                                          N                                                9.095                                                                             COOCH.sub.3                                                                          2 methyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.096                                                                             COOCH.sub.3                                                                          2 methyl  CH(OCH.sub.3)                                                                         OCH.sub.3                                                                          CH                                               9.097                                                                             COOCH.sub.3                                                                          0 4-chlorophenyl                                                                         CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.098                                                                             COOCH.sub.3                                                                          0 4-chlorophenyl                                                                         OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.099                                                                             COOCH.sub.3                                                                          0 4-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          N                                                9.100                                                                             COOCH.sub.3                                                                          0 4-chlorophenyl                                                                         N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.101                                                                             COOCH.sub.3                                                                          0 4-chlorophenyl                                                                         CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.102                                                                             COOCH.sub.3                                                                          0 4-chlorophenyl                                                                         CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.103                                                                             COOCH.sub.3                                                                          2 4-chlorophenyl                                                                         CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.104                                                                             COOCH.sub.3                                                                          2 4-chlorophenyl                                                                         OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.105                                                                             COOCH.sub.3                                                                          2 4-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          N                                                9.106                                                                             COOCH.sub.3                                                                          2 4-chlorophenyl                                                                         N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.107                                                                             COOCH.sub.3                                                                          2 4-chlorophenyl                                                                         CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.108                                                                             COOCH.sub.3                                                                          2 4-chlorophenyl                                                                         CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.109                                                                             OCHF.sub.2                                                                           0 methyl  CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.110                                                                             OCHF.sub.2                                                                           0 methyl  OCH.sub.2 CH.sub.3                                                                    OCH.sub.3                                                                          CH                                               9.111                                                                             OCHF.sub.2                                                                           0 methyl  Cl     OCH.sub.3                                                                          N                                                9.112                                                                             OCHF.sub.2                                                                           0 methyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          CH                                               9.113                                                                             OCHF.sub.2                                                                           0 methyl  CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.114                                                                             OCHF.sub.2                                                                           0 methyl  CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.115                                                                             OCHF.sub.2                                                                           2 methyl  CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.116                                                                             OCHF.sub.2                                                                           2 methyl  OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.117                                                                             OCHF.sub.2                                                                           2 methyl  Cl     OCH.sub.3                                                                          N                                                9.118                                                                             OCHF.sub.2                                                                           2 methyl  N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.119                                                                             OCHF.sub.2                                                                           2 methyl  CH(OCH.sub.3)                                                                         OCH.sub.3                                                                          CH                                               9.120                                                                             OCHF.sub.2                                                                           0 4-chlorophenyl                                                                         CH.sub.2 OCH.sub. 3                                                                   CH.sub.3                                                                           CH                                               9.121                                                                             OCHF.sub.2                                                                           0 4-chlorophenyl                                                                         OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.122                                                                             OCHF.sub.2                                                                           0 4-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          N                                                9.123                                                                             OCHF.sub.2                                                                           0 4-chlorophenyl                                                                         N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.124                                                                             OCHF.sub.2                                                                           0 4-chlorophenyl                                                                         CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.125                                                                             OCHF.sub.2                                                                           0 4-chlorophenyl                                                                         CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.126                                                                             OCHF.sub.2                                                                           2 4-chlorophenyl                                                                         CH.sub.2 OCH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.127                                                                             OCHF.sub.2                                                                           2 4-chlorophenyl                                                                         OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                           CH                                               9.128                                                                             OCHF.sub.2                                                                           2 4-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          N                                                9.129                                                                             OCHF.sub.2                                                                           2 4-chlorophenyl                                                                         N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N                                                9.130                                                                             OCHF.sub.2                                                                           2 4-chlorophenyl                                                                         CH(OCH.sub.3).sub.2                                                                   OCH.sub.3                                                                          CH                                               9.131                                                                             OCHF.sub.2                                                                           2 4-chlorophenyl                                                                         CH.sub.2 Cl                                                                           OCH.sub.3                                                                          CH                                               9.132                                                                             Cl    0 4-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          CH 142-144°                               9.133                                                                             Cl    2 4-chlorophenyl                                                                         Cl     OCH.sub.3                                                                          CH 140-142°                                                                dec.                                          9.134                                                                             COOC.sub.2 H.sub.5                                                                   0 p-tolyl Cl     OCH.sub.3                                                                          CH                                               9.135                                                                             COOC.sub.2 H.sub.5                                                                   2 p-tolyl Cl     OCH.sub.3                                                                          CH                                               9.136                                                                             COOCH.sub.3                                                                          0 2,4,5-tri-                                                                             CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH 128-130°                                          chlorophenyl          dec.                                          9.137                                                                             COOCH.sub.3                                                                          0 p-tolyl N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N  138-140°                               9.138                                                                             F     0 CH.sub.2 COOCH.sub.3                                                                   N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N  130-133°                               9.139                                                                             NO.sub.2                                                                             0 2,4,5-tri-                                                                             CH.sub.2 OCH.sub.3                                                                    OCH.sub.3                                                                          CH 118-120°                                          chlorophenyl                                                        9.140                                                                             Cl    0 CH.sub.2 COOCH.sub.3                                                                   N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N  135-138°                               9.141                                                                             COOCH.sub.3                                                                          0 CH.sub.2 COOCH.sub.3                                                                   N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N  145-148°                               9.142                                                                             CF.sub.3                                                                             2 CH.sub.3                                                                               N(CH.sub.3).sub.2                                                                     OCH.sub.3                                                                          N  171-175°                                                                dec.                                          __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________      ##STR47##                                                                     __________________________________________________________________________     No  R.sup.1                                                                              R.sup.6      R.sup.3                                                                            R.sup.4                                                                              E  m.p. (°C.)                          __________________________________________________________________________     10.001                                                                             COOCH.sub.3                                                                          benztriazol-1-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                             CH 178-180°                            10.002                                                                             COOCH.sub.3                                                                          1,2,4-triazol-1-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                             CH 164-167°                            10.003                                                                             COOCH.sub.3                                                                          2-methylbenzimidazol-1-yl                                                                   CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.004                                                                             COOCH.sub.3                                                                          2,3-dimethylindol-1-yl                                                                      CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.005                                                                             Cl    benztriazol-1-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                             CH 122-128°                                                                dec.                                       10.006                                                                             Cl    1,2,4-triazol-1-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                             CH 152-157°                                                                dec.                                       10.007                                                                             Cl    2-methylbenzimidazol-1-yl                                                                   CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.008                                                                             Cl    2,3-dimethylindol-1-yl                                                                      CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.009                                                                             OCHF.sub.2                                                                           benztriazol-1-yl                                                                            CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.010                                                                             OCHF.sub.2                                                                           1,2,4-triazol-1-yl                                                                          CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.011                                                                             OCHF.sub.2                                                                           2-methylbenzimidazol-1-yl                                                                   CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.012                                                                             OCHF.sub.2                                                                           2,3-dimethylindol-1-yl                                                                      CH.sub.3                                                                           CH.sub.3                                                                             CH                                            10.013                                                                             OCHF.sub.2                                                                           benztriazol-1-yl                                                                            CH.sub.3                                                                           OCHF.sub.2                                                                           CH 109-111°                            10.014                                                                             COOCH.sub.3                                                                          benztriazol-1-yl                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.015                                                                             COOCH.sub.3                                                                          1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.016                                                                             COOCH.sub.3                                                                          2-methylbenzimidazol-1-yl                                                                   OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.017                                                                             COOCH.sub.3                                                                          2,3-dimethylindol-1-yl                                                                      OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.018                                                                             Cl    benztriazol-1-yl                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.019                                                                             Cl    1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.020                                                                             Cl    2-methylbenzimidazol-1-yl                                                                   OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.021                                                                             Cl    2,3-dimethylindol-1-yl                                                                      OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.022                                                                             OCHF.sub.2                                                                           benztriazol-1-yl                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                            CH 144-147°                            10.023                                                                             OCHF.sub.2                                                                           1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.024                                                                             OCHF.sub.2                                                                           2-methylbenzimidazol-1-yl                                                                   OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.025                                                                             OCHF.sub.2                                                                           2,3-dimethylindol-1-yl                                                                      OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.026                                                                             OCHF.sub.2                                                                           benztriazol-1-yl                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                            CH                                            10.027                                                                             COOCH.sub.3                                                                          benztriazol-1-yl                                                                            OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.028                                                                             COOCH.sub.3                                                                          1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.029                                                                             COOCH.sub.3                                                                          2-methylbenzimidazol-1-yl                                                                   OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.030                                                                             COOCH.sub.3                                                                          2,3-dimethylindol-1-yl                                                                      OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.031                                                                             Cl    benztriazol-1-yl                                                                            OCH.sub. 3                                                                         CH.sub.3                                                                             CH                                            10.032                                                                             Cl    1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.033                                                                             Cl    2-methylbenzimidazol-1-yl                                                                   OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            __________________________________________________________________________     No  R.sup.1 (R.sup.2)                                                                    R.sup.6      R.sup.3                                                                            R.sup.4                                                                              E  m.p. (°C.)                          __________________________________________________________________________     10.034                                                                             Cl    2,3-dimethylindol-1-yl                                                                      OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.035                                                                             OCHF.sub.2                                                                           benztriazol-1-yl                                                                            OCH.sub.3                                                                          CH.sub.3                                                                             CH 154-158°                            10.036                                                                             OCHF.sub.2                                                                           1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.037                                                                             OCHF.sub.2                                                                           2-methylbenzimidazol-1-yl                                                                   OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.038                                                                             OCHF.sub.2                                                                           2,3-dimethylindol-1-yl                                                                      OCH.sub.3                                                                          CH.sub.3                                                                             CH                                            10.039                                                                             OCHF.sub.2                                                                           benztriazol-1-yl                                                                            OCH.sub.3                                                                          OCHF.sub.2                                                                           CH                                            10.040                                                                             2,6-Cl.sub.2                                                                         1,2,4-triazol-1-yl                                                                          OCH.sub.3                                                                          OCH.sub.3                                                                            CH 156-159°                            10.041                                                                             COOCH.sub.3                                                                          benztriazol-1-yl                                                                            OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                   CH 157-160°                            10.042                                                                             Cl    5(6)-nitro-benztriazol-1-yl                                                                 OCH.sub.3                                                                          OCH.sub.3                                                                            CH 152-155°                                      (mixture of isomers)                                                 10.043                                                                             F     5(6)-nitro-benztriazol-1-yl                                                                 OCH.sub.3                                                                          CH.sub.3                                                                             CH 147-149°                                      (mixture of isomers)                                                 10.044                                                                             2-Cl, 6-CH.sub.3                                                                     5(6)-Nitro-benztriazol-1-yl                                                                 OCH.sub.3                                                                          CH.sub.3                                                                             CH 131-134°                                      (mixture of isomers)                                                 __________________________________________________________________________

Formulation Examples

EXAMPLE 14 Formulation Examples for compounds of formula I (percentages are by weight)

    ______________________________________                                         (a) Wettable powders                                                                               (a)     (b)     (c)                                        ______________________________________                                         Compound of formula I                                                                              20%     60%     0.5%                                       sodium lignosulfonate                                                                              5%      5%      5%                                         sodium laurylsulfate                                                                               3%      --      --                                         sodium diisobutylnaphthalenesulfonate                                                              --      6%      6%                                         octylphenol polyethylene glycol ether                                                              --      2%      2%                                         (7-8 moles of ethylene oxide)                                                  highly dispersed silicid acid                                                                      5%      27%     27%                                        kaolin              67%     --      --                                         sodium chloride     --      --      59.5%                                      ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of the desired concentration.

    ______________________________________                                         (b) Emulsifiable concentrates                                                                         (a)    (b)                                              ______________________________________                                         Compound of formula I  10%    1%                                               octylphenol polyethylene glycol ether                                                                  3%    3%                                               (4-5 moles of ethylene oxide)                                                  calcium dodecylbenzenesulfonate                                                                        3%    3%                                               castor oil polyglycol ether                                                                            4%    4%                                               (36 moles of ethylene oxide)                                                   cyclohexanone          30%    10%                                              xylene mixture         50%    79%                                              ______________________________________                                    

Emulsions of any required concentration can be obtained from this concentrate by dilution with water.

    ______________________________________                                         (c) Dusts           (a)     (b)                                                ______________________________________                                         Compound of formula I                                                                              0.1%     1%                                                talcum              99.9%   --                                                 kaolin              --      99%                                                ______________________________________                                    

Dusts which are ready for use are obtained by mixing the active ingredient with the carriers, and grinding the mixture in a suitable mill.

    ______________________________________                                         (d) Extruder granulate                                                                             (a)    (b)                                                 ______________________________________                                         Compound of formula I                                                                              10%    1%                                                  sodium lignosulfonate                                                                               2%    2%                                                  carboxymethylcellulose                                                                              1%    1%                                                  kaolin              87%    96%                                                 ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and the mixture is subsequently moistened with water. The mixture is extruded and then dried in a stream of air.

    ______________________________________                                         (e) Coated granulate                                                           ______________________________________                                         Compound of formula                                                                               3%                                                          polyethylene glycol 200                                                                           2%                                                          kaolin             94%                                                         ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granulates are obtained in this manner.

    ______________________________________                                         (f) Suspension concentrate                                                                            (a)     (b)                                             ______________________________________                                         Compound of formula I  40%     5%                                              ethylene glycol        10%     10%                                             nonylphenol polyethylene glycol ether                                                                  6%     1%                                              (15 moles of ethylene oxide)                                                   sodium lignosulfonate  10%     5%                                              carboxymethylcellulose  1%     1%                                              37% aqueous formaldehyde solution                                                                     0.2%    0.2%                                            silicone oil in the form of a 75%                                                                     0.8%    0.8%                                            aqueous emulsion                                                               water                  32%     77%                                             ______________________________________                                    

The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.

    ______________________________________                                         (g) Salt solution                                                              ______________________________________                                         Compound of formula I  5%                                                      isopropylamine         1%                                                      octylphenol polyethylene glycol ether                                                                 3%                                                      (78 moles of ethylene oxide)                                                   water                  91%                                                     ______________________________________                                    

Biological Examples

EXAMPLE 15 Preemergence herbicidal action

Plastic pots are filled with expanded vermiculite (density: 0.135 g/cm³, water-absorbing capacity: 0.565 l/l). After the non-absorptive vermiculite has been saturated with an aqueous emulsion in deionised water which contains the test compound in a concentration of 70.8 ppm, seeds of the following plants are sown on the surface: Nasturtium officinalis, Agrostis tenuis, Stellaria media and Digitaria sanguinalis. The pots are then kept in a climatic chamber at 20° C., an illumination of about 20 lux and a relative humidity of 70%. During the germinating phase of 4 to 6 days, the pots are covered with lightpermeable material and watered with deionised water to increase the local humidity. After the 5th day, 0.5% of a commercial liquid fertiliser (Greenzit®, ex Ciba-Geigy) is added to the water. The test is evaluated 12 days after sowing and the action on the plants is assessed according to the following rating:

    ______________________________________                                         1       plants have not emerged or are totally withered                        2-3     very pronounced action                                                 4-6     medium action                                                          7-8     weak action                                                            9       no action (as untreated controls).                                     ______________________________________                                    

Preemergence action:

Concentration of the test compound emulsion: 70.8 ppm

    ______________________________________                                         Test plant                                                                     Compound                                                                               Nasturtium  Stellaria                                                                               Agrostis Digitaria                                ______________________________________                                         5.001   2           2        2        2                                        5.004   1           1        1        1                                        5.007   1           1        1        1                                        5.022   2           2        2        2                                        5.051   2           2        2        2                                        5.061   2           2        2        2                                        5.064   1           1        1        1                                        5.066   1           1        1        1                                        5.089   2           1        1        2                                        5.102   2           1        1        2                                        5.105   1           1        1        1                                        5.107   1           1        1        1                                        5.121   2           2        2        2                                        5.124   2           2        2        2                                        5.130   2           2        2        2                                        5.133   2           2        2        2                                        5.142   2           2        2        2                                        5.165   1           2        1        2                                        5.170   2           2        2        2                                        5.229   2           2        2        2                                        5.230   2           2        2        2                                        5.231   2           2        2        2                                        5.232   2           1        1        2                                        5.235   2           2        2        2                                        5.236   2           1        1        2                                        5.237   2           2        2        2                                        5.238   2           1        2        2                                        5.239   2           1        1        1                                        5.240   2           2        2        2                                        5.241   2           2        2        2                                        5.242   2           2        2        2                                        5.243   2           3        2        3                                        5.244   2           3        2        3                                        5.246   3           4        3        5                                        5.247   3           5        3        5                                        5.252   2           2        2        2                                        6.001   2           2        2        2                                        6.010   1           1        1        1                                        6.011   1           1        1        1                                        6.013   2           2        2        2                                        6.021   2           2        2        2                                        6.040   2           2        2        2                                        6.041   2           2        2        2                                        6.061   2           1        2        1                                        6.230   2           2        3        3                                        6.233   3           4        4        5                                        6.240   3           3        3        3                                        6.242   2           2        2        2                                        6.245   1           1        1        1                                        6.253   1           1        1        1                                        6.254   1           1        1        1                                        6.267   2           2        2        2                                        6.268   1           1        1        1                                        6.269   2           2        2        2                                        6.270   2           2        2        2                                        7.001   1           1        1        1                                        7.061   1           1        1        1                                        7.082   2           2        2        2                                        7.084   2           2        2        2                                        7.141   2           2        2        3                                        7.142   2           2        2        2                                        7.229   4           5        4        5                                        7.230   2           1        1        2                                        7.231   2           2        2        3                                        7.232   2           2        2        3                                        7.234   2           2        2        3                                        7.236   2           2        2        2                                        7.237   2           1        1        1                                        8.004   2           2        2        2                                        8.025   2           1        2        1                                        8.067   2           2        2        2                                        8.097   2           2        2        2                                        9.026   1           1        1        2                                        9.049   2           2        2        2                                        9.083   2           2        2        2                                        9.085   2           1        1        2                                        9.132   1           1        1        2                                        9.133   1           1        1        2                                        9.139   2           2        2        2                                        9.140   1           1        1        2                                        9.141   1           1        1        1                                        10.001  2           2        2        2                                        10.002  2           2        1        2                                        10.005  2           2        4        5                                        10.006  2           2        2        2                                        10.013  2           3        2        4                                        10.022  2           2        1        2                                        10.035  2           2        2        2                                        10.040  2           2        2        2                                        10.041  2           2        2        2                                        10.042  2           3        2        3                                        10.043  2           2        2        2                                        10.044  2           2        2        2                                        ______________________________________                                    

EXAMPLE 16 Growth inhibition of tropical cover crops

The test plants (centrosema plumieri and centrosema pubescens) are reared until fully grown and then cut back to a height of 60 cm. The plants are sprayed 7 days later with an aqueous emulsion of the test compound. The test plants are kept at 70% relative humidity and 6000 lux artificial light for 14 hours per day, at day temperatures of 27° C. and night temperatures of 21° C. and night temperatures of 21° C. The test is evaluated 4 weeks after application by assessing and weighing the new growth compared with controls and by determining the phytotoxicity.

In this test a marked reduction in new growth of the plants treated with compounds of the formula I is observed (less than 20% of the new growth of untreated control plants), without damage being caused to the test plants.

EXAMPLE 17 Growth regulation of soybeans

Soybeans of the "Hark" variety are sown in plastic containers in an earth/peat/sand mixture (6:3:1). The containers are put into a climatic chamber and the plants develop to the 5-6 trefoil leaf stage after about 5 weeks by optimum control of temperature, light, fertiliser addition, and watering. The plants are then sprayed with an aqueous mixture of a compound of the formula I until thoroughly wetted. The rate of application corresponds to 100 g a.i. per hectare. Evaluation is made about 5 weeks after application. Compared with untreated controls, the compounds of the formula I markedly increase the number and weight of the harvested siliques on the leading shoot.

EXAMPLE 18 Growth inhibition of cereals

Summar barley (Hordeum vulgare) and summer rye (Secale) are sown in sterilised soil in plastic beakers in a greenhouse and watered as required. The cereal shoots are treated about 21 days after sowing with an aqueous spray mixture of a compound of the formula I. The concetration corresponds to 100 g of active ingredient per hectare. Evaluation of the growth of the cereals is made 21 days after application. A comparison with untreated controls shows that the growth of cereal plants treated with compounds of the formula I is significantly reduced (60-90% of the controls) and that the diameter of the stalks has in some cases increased.

EXAMPLE 19 Growth inhibition of grasses

Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylis glomerate and Cynodon dactylon are sown in plastic dishes filled with an earth/peat/sand mixture (6:3:1), in a greenhouse, and watered as required. The emergent grasses are cut back weekly to a height of 4 cm, and about 50 days after sowing and 1 day after the last cut are sprayed with an aqueous spray mixture of a compound of the formula I. The concentration of test compound corresponds to a rate of application of up to 100 g a.i. per hectare. The growth of the grasses is evaluated 21 days after application. The compounds of formula I effect a reduction in new growth in the range of 10-30% in comparison with untreated controls.

EXAMPLE 20 Root growth

To determine the stimulation of root growth, seeds which have been dressed with 45-500 mg of active ingredient per kg of seeds as well as untreated seeds for use as controls are propagated in plastic cylinders of 5 cm diameter and 30 cm in height. 10 seeds are propagated in each cylinder. The cylinders are kept in climatic chambers under controlled conditions. Evaluation of the test is made 10 days after sowing and after carefully washing off the soil. The length and dry weight of the roots are determined and compared with the results obtained with untreated seeds.

Compared with untreated seedlings, wheat seeds treated with 100 and 200 mg of active ingredient per kg of seeds exhibited an approximately 10% increase in length and weight. 

What is claimed is:
 1. An N-pyrimidinyl-methylamine of the formula ##STR48## wherein G is selected from R⁶ and R⁹ S(O)_(m) m is 0 or 2 E is --CH═, R³ is halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₂ -C₄ alkoxyalkyl, C₂ -C₄ alkoxyalkoxy, cyclopropyl, --NH₂, C₁ -C₄ alkylamino or di(C₁ -C₄ alkyl)amino, R⁴ has the same meaning as R³ but independently thereof, R⁵ is hydrogen or C₁ -C₄ alkyl, R⁶ is a 5- to 7-membered heterocyclic radical which is bound through the nitrogen atom and which may be fused to a benzene ring, which is selected from among 1,2,4-triazole, benztriazole, benzimidazole, carbazole, indole, imidazole and pyrazole, which is unsubstituted or substituted by one or more members selected from the group consisting of nitro, halogen, and C₁ -C₄ alkyl, R⁹ is C₁ -C₄ alkyl which is unsubstituted or substituted by halogen, C₂ -C₄ alkoxy, carboxyl, C₁ -C₄ alkoxycarbonyl or --CONR¹⁰ R¹¹, or is a phenyl, benzyl or naphthyl radical, each of which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of halogen, nitro, carboxyl, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy or C₁ -C₄ haloalkoxy, and R⁹ can also be a radical selected from --CZ--C₁ -C₄ alkyl, --CZO--C₁ -C₄ alkyl, --CZNR¹⁰ R¹¹, --CZ-phenyl, CZ-benzyl or CZ-naphthyl, wherein the phenyl rings may be substituted as indicated above, R¹⁰ and R¹¹, each independently of the other, are hydrogen, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₁ -C₄ cyanoalkyl, or one of R¹⁰ and R¹¹ may also be C₁ -C₄ alkoxy or C₂ -C₄ alkoxyalkyl, phenyl or benzyl, and the penyl ring may be substituted by one or more identical or different members selected from the group consisting of halogen, nitro, C₁ -C₄ haloalkyl or C₁ -C₄ alkoxy; or R¹⁰ and R¹¹, together with the nitrogen atom to which they are attached, may also be a 5- to 7-membered saturated heterocycle selected from among pyrrolidine, piperidine, morpholine and azepine and which are unsubstituted or substituted by halogen or C₁ -C₄ alkyl and Z is oxygen or sulfur.
 2. An N-pyrimidinyl-N-thiomethylamino or -sulfonylamine of the formula ##STR49## wherein E, m, R³ R⁴ and R⁹ are as defined in claim
 1. 3. An N-pyrimidinyl-heterocyclylaminomethylamine of the formula ##STR50## wherein R⁵, R⁶, E R³ and R⁴ are as defined in claim
 1. 4. N-(4,6-dimethylpyrimidin-2-yl)-N-(4-chlorophenylthiomethyl)amine, according to claim
 1. 5. N-(4-difluoromethoxy-6-methylpyrimidin-2-yl)-N-(4-tolylsulfonylmethyl)amine, according to claim
 1. 6. N-(4-methoxy-5-methylpyrimidin-2-yl)-N-(naphthylthiomethyl)amine, according to claim
 1. 7. N-(4,6-dimethylpyrimidin-2-yl)-N-pyrrolidinothiocarbonylthiomethyl)amine, according to claim
 1. 8. N-(4,6-dimethylpyrimidin-2-yl)-N-(4-tolylsulfonylmethyl)amine, according to claim
 1. 9. N-(4methoxy-6-methylpyrimidin-2-yl)-N-(4-tolylsulfonylmethyl)amine, according to claim
 1. 10. N-(4,6-dimethylpyrimidin-2-yl)-N-(1,2,4-triazol-1-yl-methyl)amine, according to claim
 1. 